Synthesis and stereochemistry of the four isomeric pinane-2,3-diols
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(20)
, 3437-3449. https://doi.org/10.1021/acs.organomet.8b00163
- Julia M. Clay, Dusan Hesek, Allen G. Oliver, Mijoon Lee, and Jed F. Fisher . Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal. The Journal of Organic Chemistry 2016, 81
(13)
, 5705-5709. https://doi.org/10.1021/acs.joc.6b00756
- Liliya E. Nikitina, Svetlana A. Lisovskaya, Valeriya A. Startseva, Larisa L. Frolova, Alexander V. Kutchin, Oksana G. Shevchenko, Olga V. Ostolopovskaya, Roman S. Pavelyev, Mohammed A. Khelkhal, Ilmir R. Gilfanov, Inna V. Fedyunina, Renad R. Khaliullin, Rustem F. Akhverdiev, Alexander V. Gerasimov, Ekaterina V. Abzaldinova, Alexander G. Izmailov. Biological Activity of Bicyclic Monoterpene Alcohols. BioNanoScience 2021, 11
(4)
, 970-976. https://doi.org/10.1007/s12668-021-00912-8
- O.A. Zalevskaya, Y.A. Gur'eva, A.V. Kutchin, Yu.R. Aleksandrova, E.Yu. Yandulova, N.S. Nikolaeva, M.E. Neganova. Palladium complexes with terpene derivatives of ethylenediamine and benzylamine: Synthesis and study of antitumor properties. Inorganica Chimica Acta 2021, 527 , 120593. https://doi.org/10.1016/j.ica.2021.120593
- Yana A. Gur'eva, Igor N. Alekseev, Irina A. Dvornikova, Olga A. Zalevskaya, Aleksandr V. Kuchin. Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one. Inorganica Chimica Acta 2018, 477 , 300-305. https://doi.org/10.1016/j.ica.2018.03.015
- Robert K. Boeckman, Jeremy A. Cody. Synthesis and Utility of Heteroand Non-heterocyclic Chiral Auxiliaries Derived from Terpenes: Camphor and Pinene. 2018, 193-251. https://doi.org/10.1007/7081_2017_12
- Ivan S. Kondratov, Ivan G. Logvinenko, Nataliya A. Tolmachova, Roman N. Morev, Maria A. Kliachyna, Florian Clausen, Constantin G. Daniliuc, Günter Haufe. Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid – a CF
3
O-containing analogue of natural lipophilic amino acids. Organic & Biomolecular Chemistry 2017, 15
(3)
, 672-679. https://doi.org/10.1039/C6OB02436J
- Ramalingam Boobalan, You‐Ming Chang, Chinpiao Chen, Gene‐Hsian Lee. Copper Complex of Pinene based Schiff base [CuSBADBH]
2
: Synthesis and its Application in Catalytic Asymmetric Nitroaldol (Henry) Reaction. ChemistrySelect 2016, 1
(9)
, 2028-2034. https://doi.org/10.1002/slct.201600359
- Ya. A. Gur’eva, I. N. Alekseev, O. A. Zalevskaya, P. A. Slepukhin, A. V. Kutchin. Synthesis of new bidentate ligands—terpene derivatives of ethylenediamine and their palladium complexes. Russian Journal of Organic Chemistry 2016, 52
(6)
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- Dirk Ulbrich, Constantin G. Daniliuc, Günter Haufe. Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline. Organic & Biomolecular Chemistry 2016, 14
(9)
, 2755-2767. https://doi.org/10.1039/C6OB00131A
- I. A. Dvornikova, E. V. Buravlev, K. Yu. Suponitskii, I. Yu. Chukicheva, A. V. Kutchin. Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction. Russian Journal of Organic Chemistry 2015, 51
(4)
, 480-492. https://doi.org/10.1134/S1070428015040041
- Ya. A. Gur′eva, O. A. Zalevskaya, I. N. Alekseev, L. L. Frolova, P. A. Slepukhin, A. V. Kuchin. New Optically Active CN-Palladacycles Based on 2α-Hydroxypinan-3-One and Camphor Derivatives. Chemistry of Natural Compounds 2014, 50
(4)
, 648-651. https://doi.org/10.1007/s10600-014-1044-3
- L. L. Frolova, A. V. Popov, L. V. Bezuglaya, I. N. Alekseev, P. A. Slepukhin, A. V. Kuchin. Oxidation of terpenoid diols with chlorine dioxide. Easy preparation of α-hydroxyketones. Russian Journal of General Chemistry 2014, 84
(5)
, 853-859. https://doi.org/10.1134/S1070363214050120
- L. L. Frolova, A. V. Popov, L. V. Bezuglaya, I. N. Alekseev, P. A. Slepukhin, A. V. Kuchin. Oxidation of terpenoid diols with chlorine dioxide: Preparation of ketols and α-chlorohydroxyketones of carane and pinane structures. Russian Journal of General Chemistry 2013, 83
(8)
, 1541-1547. https://doi.org/10.1134/S1070363213080124
- A. V. Kuchin, Ya. A. Gur’eva, L. L. Frolova, I. N. Alekseev, O. A. Zalevskaya. New chiral cyclopalladated complexes based on the pinane and bornane imines. Russian Chemical Bulletin 2013, 62
(3)
, 745-750. https://doi.org/10.1007/s11172-013-0101-6
- Ghaita Chahboun, Jose Angel Brito, Beatriz Royo, Mohamed Amin El Amrani, Enrique Gómez‐Bengoa, Marta E. G. Mosquera, Tomás Cuenca, Eva Royo. Olefin Epoxidation Catalyzed by
cis
‐Dioxdomolybdenum(VI) Complexes Containing Chiral Alkoxo‐Imino Ligands Derived from (+)‐α‐Pinene. European Journal of Inorganic Chemistry 2012, 2012
(17)
, 2940-2949. https://doi.org/10.1002/ejic.201200144
- J.A. Cody, R.K. Boeckman. 3.3 Terpene Derived Auxiliaries: Camphor and Pinene Derived Auxiliaries. 2012, 42-105. https://doi.org/10.1016/B978-0-08-095167-6.00303-7
- Dennis Hobuß, Jens Hasenjäger, Birgit Driessen-Hölscher, Angelika Baro, Kirill V. Axenov, Sabine Laschat, Wolfgang Frey. Novel α-pinene-derived mono- and bisphosphinite ligands: Synthesis and application in catalytic hydrogenation. Inorganica Chimica Acta 2011, 374
(1)
, 94-103. https://doi.org/10.1016/j.ica.2011.01.020
- I. A. Dvornikova, E. V. Buravlev, L. L. Frolova, Yu. V. Nelyubina, I. Yu. Chukicheva, A. V. Kuchin. Synthesis of 1,2-diamine ligands based on natural monoterpenoids. Russian Journal of Organic Chemistry 2011, 47
(8)
, 1130-1138. https://doi.org/10.1134/S1070428011080021
- Ya. A. Gur’eva, O. A. Zalevskaya, L. L. Frolova, I. N. Alekseev, A. V. Kuchin. Chiral imines and amines based on 2-hydroxypinan-3-one. Chemistry of Natural Compounds 2011, 46
(6)
, 920-923. https://doi.org/10.1007/s10600-011-9783-x
- Mohammed Samir Ibn Elalami, Abdel Aziz Dahdouh, Ahmed Ibn Mansour, Mohammed Amin ElAmrani, Isabelle Suisse, André Mortreux, Francine Agbossou-Niedercorn. Synthesis of chiral bifunctional ligands based on α-pinene and their use in ruthenium catalyzed asymmetric transfer hydrogenation. Comptes Rendus. Chimie 2009, 12
(12)
, 1253-1258. https://doi.org/10.1016/j.crci.2009.02.003
- Dennis Hobuß, Angelika Baro, Sabine Laschat, Wolfgang Frey. Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols. Tetrahedron 2008, 64
(8)
, 1635-1640. https://doi.org/10.1016/j.tet.2007.12.020
- Konstantin N. Gavrilov, Eduard B. Benetsky, Tatiana B. Grishina, Sergey V. Zheglov, Eugenie A. Rastorguev, Pavel V. Petrovskii, Fliur Z. Macaev, Vadim A. Davankov. Diastereomeric P∗-chiral diamidophosphites with terpene fragments in asymmetric catalysis. Tetrahedron: Asymmetry 2007, 18
(21)
, 2557-2564. https://doi.org/10.1016/j.tetasy.2007.10.022
- Kyoungwon Kim, Joosung Kang, Seungyong Kim, Suhang Choi, Sejin Lim, Chaeuk Im, Chulbu Yim. Synthesis and cytotoxicity of new aromatic ceramide analogs with alkylsulfonamido chains. Archives of Pharmacal Research 2007, 30
(5)
, 570-580. https://doi.org/10.1007/BF02977651
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. 2‐Hydroxypinan‐3‐one. 2006https://doi.org/10.1002/9780471264194.fos05757
- Kyung-Ho Park, Mark J. Kurth. Cyclic amino acid derivatives. Tetrahedron 2002, 58
(43)
, 8629-8659. https://doi.org/10.1016/S0040-4020(02)00989-4
- Stanisław W. Markowicz, Katarzyna Pokrzeptowicz, Janina Karolak-Wojciechowska, Robert Czylkowski, Jan Omelańczuk, Agata Sobczak. Enantiomerically pure α-pinene derivatives from material of 65% enantiomeric purity. Part 1: Di[3α-(2α-hydroxy)pinane]amine. Tetrahedron: Asymmetry 2002, 13
(18)
, 1981-1991. https://doi.org/10.1016/S0957-4166(02)00512-8
- K. M. Höld, N. S. Sirisoma, S. E. Sparks, J. E. Casida. Metabolism and mode of action of
cis
- and
trans
-3-pinanones (the active ingredients of hyssop oil). Xenobiotica 2002, 32
(4)
, 251-265. https://doi.org/10.1080/00498250110095745
- Braja G. Hazra, Vandana S. Pore, Mahendra D. Chordia, Bharat B. Bahule, Sourav Basu. Vicinal Dihydroxylation of Alkenes with Tetradecyltrimethylammonium permanganate and potassium hydroxide in a two phase Solvent System. Journal of Chemical Research 2001, 2001
(11)
, 500-502. https://doi.org/10.3184/030823401103168659
- Tobias Rein. (1
S
,2
S
,5
S
)-2-Hydroxypinan-3-one. 2001https://doi.org/10.1002/047084289X.rh063
- Klaus W. Laue, Stefan Kröger, Elina Wegelius, Günter Haufe. Stereoselective Synthesis of γ-Fluorinated α-Amino Acids Using 2-Hydroxy-3-pinanone as an Auxiliary. European Journal of Organic Chemistry 2000, 2000
(22)
, 3737-3743. https://doi.org/10.1002/1099-0690(200011)2000:22<3737::AID-EJOC3737>3.0.CO;2-A
- Yilin Song, Quanrui Wang, Zongbiao Ding, Fenggang Tao. Synthesis of Hydroxycedranone and Aminohydroxycedrane. Synthetic Communications 1999, 29
(23)
, 4171-4178. https://doi.org/10.1080/00397919908085890
- Yu-Hung Chiu, Osvaldo dos Santos, James W Canary. Conformational control of propeller-like chirality in Zn(II) complexes: Tightly balanced steric bias. Tetrahedron 1999, 55
(41)
, 12069-12078. https://doi.org/10.1016/S0040-4020(99)00713-9
- S. Bouifraden, C. Drouot, M. El Hadrami, F. Guenoun, L. Lecointe, N. Mai, M. Paris, C. Pothion, M. Sadoune, B. Sauvagnat, M. Amblard, J. L. Aubagnac, M. Calmes, P. Chevallet, J. Daunis, C. Enjalbal, J. A. Fehrentz, F. Lamaty, J. P. Lavergne, R. Lazaro, V. Rolland, M. L. Roumestant, Ph. Viallefont, Y. Vidal, J. Martinez. Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins. Amino Acids 1999, 16
(3-4)
, 345-379. https://doi.org/10.1007/BF01388176
- Jason H. Swango, Balwinder S. Bhatti, Muhammad M. Qureshi, Peter A. Crooks. A novel enantioselective synthesis of (S)-(?)- and (R)-(+)-nornicotine via alkylation of a chiral 2-hydroxy-3-pinanone ketimine template. Chirality 1999, 11
(4)
, 316-318. https://doi.org/10.1002/(SICI)1520-636X(1999)11:4<316::AID-CHIR9>3.0.CO;2-D
- S. Hannour, A. Ryglowski, M.L. Roumestant, Ph. Viallefont, J. Martinez, F. Ouazzani, A. El Hallaoui. Enantiospecific Synthesis of α-Amino Phosphonic Acids. Phosphorus, Sulfur, and Silicon and the Related Elements 1998, 134
(1)
, 419-430. https://doi.org/10.1080/10426509808545483
- Venkat Krishnamurthy, John J. Landi, Gregory P. Roth. A Convenient Large Scale Synthesis of 2-Hydroxy-3-pinanone. Synthetic Communications 1997, 27
(5)
, 853-860. https://doi.org/10.1080/00397919708004206
- Naoko Irako, Yasumasa Hamada, Takayuki Shioiri. A New Asymmetric Synthesis of (S)-Dolaphenine and Its Heteroaromatic Congeners Utilizing (+)-2-Hydroxy-3-pinanone and (−)-3-Hydroxy-2-caranone as Chiral Auxiliaries. Tetrahedron 1995, 51
(46)
, 12731-12744. https://doi.org/10.1016/0040-4020(95)00828-V
- Moriyasu Masui, Takayuki Shioiri. A practical method for preparation of optically pure oxazaborolidines from α-Pinene. Tetrahedron 1995, 51
(30)
, 8363-8370. https://doi.org/10.1016/0040-4020(95)00447-G
- Arlette Solladié-Cavallo, Johannes Schwarz, Vincent Burger. A four-step, highly enantioselective synthesis and enzymatic resolution of 3,4-dichloro-phenylalanine.. Tetrahedron: Asymmetry 1994, 5
(8)
, 1621-1626. https://doi.org/10.1016/0957-4166(94)80133-9
- Liu Shikui, Mi Aiqiao, Wu Lanjun, Jiang Yaozhong. Asymmetric Synthesis. XVIII. Stereocontrolled Synthesis of α-Substituted-2-furfurylamines via Chiral Intermediates. Synthetic Communications 1993, 23
(17)
, 2485-2488. https://doi.org/10.1080/00397919308011135
- Florine Cavelier, Sylvie Gomez, Robert Jacquier, Jean Verducci. Deracemization of silyl enol ethers. Tetrahedron: Asymmetry 1993, 4
(12)
, 2501-2505. https://doi.org/10.1016/S0957-4166(00)82229-6
- Ai‐Qiao Mi, Zeng‐Xin Ma, Lan‐Jun Wu, Yao‐Zhong Jiang. Asymmetric syntheses of α‐amino acids via double chiral induction in alkylation of the ketimine derived from 2‐hydroxypinan‐3‐one and menthyl glycinate. Chinese Journal of Chemistry 1992, 10
(5)
, 434-438. https://doi.org/10.1002/cjoc.19920100509
- Alan F. Thomas, Florence Rey. The Baeyer-Villiger reaction of pinanones (bicyclo[3.1.1]heptanones). Tetrahedron 1992, 48
(10)
, 1927-1942. https://doi.org/10.1016/S0040-4020(01)88515-X
- Mi Aiquiao, Xiao Xun, Wu Lanjun, Jiang Yaozhong. Asymmetric Synthesis XV: Enantioselective Syntheses of (R) or (S) —α—Substituted— (2 — Pyridyl) Methylamines Via Chiral Pinanone Ketimine Template. Synthetic Communications 1991, 21
(21)
, 2207-2212. https://doi.org/10.1080/00397919108055455
- J. D. Connolly, R. A. Hill. Monoterpenoids. 1991, 7-152. https://doi.org/10.1007/978-1-4899-4513-6_2
- A. Brian Jones. Oxidation Adjacent to CX Bonds by Hydroxylation Methods. 1991, 151-191. https://doi.org/10.1016/B978-0-08-052349-1.00186-4
- Ai‐Qiao Mi, Yuan‐Wei Chen, Jing Wang, Gui‐Shu Yang, Yao‐Zhong Jiang. Asymmetric carbonyl addition with the homochiral ketimine derived from (+) or (−)‐pinanone and benzylamine. Chinese Journal of Chemistry 1990, 8
(6)
, 561-567. https://doi.org/10.1002/cjoc.19900080612
- Y.-S. Ding, C.-Y Shiue, J.S. Fowler, A.P. Wolf, A. Plenevaux. No-carrier-added (NCA) aryl [18F]fluorides via the nucleophilic aromatic substitution of electron-rich aromatic rings. Journal of Fluorine Chemistry 1990, 48
(2)
, 189-206. https://doi.org/10.1016/S0022-1139(00)80432-7
- S. S. Koval'skaya, N. G. Kozlov, M. G. Novikova, S. V. Shavyrin. Transformations of 2?-hydroxy-2,6,6-trimethylbicyclo[3.1.1]-heptan-3-one under conditions of acid catalysis. Chemistry of Natural Compounds 1990, 26
(1)
, 28-32. https://doi.org/10.1007/BF00605194
- Mi Aiqiao, Wang Jing, Chen Yuanwei, Yang Guishu, Jiang Yaozhong. Asymmetric Synthesis IX: Stereocontrolled Synthesis of (R)-or-(S)-2-amino-2-phenylethanol Via Chiral Pinanone Ketimine Template. Synthetic Communications 1989, 19
(19)
, 3337-3342. https://doi.org/10.1080/00397918908052737
- Janina Karolak-Wojciechowska, Witold Kwiatkowski, Stanislaw Wojciech Markowicz. 2?-Hydroxy-3?-[N-alkyl(aryl)]-pinanoamines. Part II. Synthesis and the nature of some pinanoamines and crystal and molecular structure of 2?-hydroxy-3?-(N-n-butyl)-pinanoamine hydrochloride. Journal of Crystallographic and Spectroscopic Research 1989, 19
(5)
, 893-903. https://doi.org/10.1007/BF01185355
- Stanislaw Wojciech Markowicz, Janina Karolak-Wojciechowska, Witold Kwiatkowski. 2?-Hydroxy-3?-[N-alkyl(aryl)]pinanoamines. Part I. Preparation and nature of some Schiff bases of 2?-hydroxypinan-3-one. Crystal and molecular structure of ?-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hepta-3-ylidenaminobenzene. Journal of Crystallographic and Spectroscopic Research 1989, 19
(3)
, 535-545. https://doi.org/10.1007/BF01185389
- Chen Yuanwei, Mi Aiqiao, Xiao Xun, Jiang Yaozhong. Asymmetric Synthesis VIII: Enantioselective Synthesis of (R) or (S)-α-Substituted Benzylamines VIA Chiral Pinanone Ketimine Template. Synthetic Communications 1989, 19
(7-8)
, 1423-1430. https://doi.org/10.1080/00397918908054552
- Jiang Yaozhong, Zhou Changyou, Piao Huri. Asymmetric Synthesis. VII. Double Stereodifferentiation in Allylation of Ketimines Bearing Two Chiral Auxiliaries. Application to Enantioselective Synthesis of α-Allylglycine. Synthetic Communications 1989, 19
(5-6)
, 881-888. https://doi.org/10.1080/00397918908051007
- Robert Jacquier, Fouad Ouazzani, Marie-louise Roumestant, Philippe Viallefont. SYNTHESIS OF ENANTIOMERICALLY PURE AMINOPHOSPHONIC ACIDS. Phosphorous and Sulfur and the Related Elements 1988, 36
(1-2)
, 73-77. https://doi.org/10.1080/03086648808079000
- Dieter Seebach, Albert K. Beck, René Imwinkelzied, Silvio Roggo, Anne Wonnacott. Chirale Alkoxytitan(IV)‐Komplexe für enantioselektive nucleophile Additionen an Aldehyde und als
Lewis
‐Säuren in
Diels‐Alder
‐Reaktionen. Helvetica Chimica Acta 1987, 70
(4)
, 954-974. https://doi.org/10.1002/hlca.19870700406
- Ulrich Schöllkopf, Rainer Schütze. Asymmetrische Synthese von α‐Aminophosphonsäuren, III. Asymmetrische Synthese von (
S
)‐(1‐Aminoalkyl)phosphonsäure‐diethylestern unter Verwendung von (+)‐Campher als chiralem Hilfsreagens. Liebigs Annalen der Chemie 1987, 1987
(1)
, 45-49. https://doi.org/10.1002/jlac.198719870108
- Yuhsuke Kawakami, Toshiki Aoki, Yuya Yamashita. Enantioface-differentiating Addition of Butyllithium to Acetophenone by the Use of (1
S
,2
S
,5
S
)-3-[(
S
)-2-Methoxy-1-alkylethylimino]-2-pinanols as Chiral Ligands. Bulletin of the Chemical Society of Japan 1985, 58
(4)
, 1329-1330. https://doi.org/10.1246/bcsj.58.1329
- Donald S. Matteson, Kizhakethil Mathew Sadhu, Rahul Ray, Pradipta K. Jesthi, Mark L. Peterson, Debesh Majumdar, David J.S. Tsai, Gerald D. Hurst, Ender Erdik. Directed asymmetric synthesis with boronic esters. Journal of Organometallic Chemistry 1985, 281
(1)
, 15-23. https://doi.org/10.1016/0022-328X(85)87086-8
- Nobuto Minowa, Masao Hirayama, Shunzo Fukatsu. Asymmetric synthesis of (+)-phosphinothricin and (+)-2-amino-4-phosphonobutyric acid. Tetrahedron Letters 1984, 25
(11)
, 1147-1150. https://doi.org/10.1016/S0040-4039(01)91546-1
- Thomas Herold, Ursula Schrott, Reinhard W. Hoffmann, G. Schnelle, W. Ladner, K. Steinbach. Stereoselektive Synthese von Alkoholen, VI
1)
Asymmetrische Synthesen von 4‐Penten‐2‐ol über Allylboronsäureester chiraler Glycole. Chemische Berichte 1981, 114
(1)
, 359-374. https://doi.org/10.1002/cber.19811140138
- Rahul Ray, Donald S. Matteson. Osmium tetroxide catalyzed hydroxylation of hindered olefins. Tetrahedron Letters 1980, 21
(5)
, 449-450. https://doi.org/10.1016/S0040-4039(00)71429-8
- W. Reischl, E. Zbiral. Zur oxidation von olefinen mit triphenylmethylphosphoniumpermanganat. Tetrahedron 1979, 35
(9)
, 1109-1110. https://doi.org/10.1016/S0040-4020(01)93730-5
- Tatsuya Shono, Ikuzo Nishiguchi, Tsunenori Yokoyama, Masahiro Nitta. A NOVEL SYNTHESIS OF
l
-CARVONE FROM
l
-α-PINENE. Chemistry Letters 1975, 4
(5)
, 433-436. https://doi.org/10.1246/cl.1975.433
- Rolf Haller, Hans J. Schneider. Asymmetrische Reduktionen, II. Reduktion von (Diphenylmethyl)alkylketonen mit Komplexen aus Lithiumalanat und
cis
‐2,3‐Pinandiol. Chemische Berichte 1973, 106
(4)
, 1312-1318. https://doi.org/10.1002/cber.19731060429