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Anti-Cram selective reduction of acyclic ketones via electron transfer initiated processes

Cite this: J. Am. Chem. Soc. 1988, 110, 13, 4475–4476
Publication Date (Print):June 1, 1988
https://doi.org/10.1021/ja00221a093
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This article is cited by 20 publications.

  1. Byung Chul Kang, Dong Guk Nam, Geum-Sook Hwang, and Do Hyun Ryu . Catalytic Asymmetric Formal Insertion of Aryldiazoalkanes into the C–H Bond of Aldehydes: Synthesis of Enantioenriched Acyclic α-Tertiary Aryl Ketones. Organic Letters 2015, 17 (19) , 4810-4813. https://doi.org/10.1021/acs.orglett.5b02370
  2. Jared W. Rigoli, Ilia A. Guzei, and Jennifer M. Schomaker . Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines. Organic Letters 2014, 16 (6) , 1696-1699. https://doi.org/10.1021/ol5003576
  3. Yongquan Sun, Binxun Yu, Xiaolei Wang, Shibing Tang, Xuegong She and Xinfu Pan. Stereoselective Syntheses of Four Diastereomers of 3,9,12-Trihydroxycalamenene via a Benzobicyclo[3.3.1] Intermediate. The Journal of Organic Chemistry 2010, 75 (12) , 4224-4229. https://doi.org/10.1021/jo1008349
  4. Melissa L. McIntosh, Cameron M. Moore and Timothy B. Clark. Copper-Catalyzed Diboration of Ketones: Facile Synthesis of Tertiary α-Hydroxyboronate Esters. Organic Letters 2010, 12 (9) , 1996-1999. https://doi.org/10.1021/ol100468f
  5. Kristine A. Nolin,, Jennifer R. Krumper,, Michael D. Pluth,, Robert G. Bergman, and, F. Dean Toste. Analysis of an Unprecedented Mechanism for the Catalytic Hydrosilylation of Carbonyl Compounds. Journal of the American Chemical Society 2007, 129 (47) , 14684-14696. https://doi.org/10.1021/ja074477n
  6. Tetsuya Aoyama,, Toshihiko Satoh,, Mari Yonemoto,, Jun Shibata,, Katsumasa Nonoshita,, Sachie Arai,, Kumiko Kawakami,, Yoshikazu Iwasawa,, Hideki Sano,, Kenji Tanaka,, Yoshiaki Monden,, Tsutomu Kodera,, Hiroharu Arakawa,, Ikuko Suzuki-Takahashi,, Toshio Kamei, and, Koji Tomimoto. A New Class of Highly Potent Farnesyl Diphosphate-Competitive Inhibitors of Farnesyltransferase. Journal of Medicinal Chemistry 1998, 41 (2) , 143-147. https://doi.org/10.1021/jm970540f
  7. U. Wille. 8.06 Reduction of CX to CHXH by Dissolving Metals and Related Methods. 2014,,, 300-316. https://doi.org/10.1016/B978-0-08-097742-3.00808-9
  8. . References. 2007,,, 315-356. https://doi.org/10.1002/9783527615698.refs
  9. Min-ah Kim, Jong Yup Kim, Kwang-Seop Song, Jeongmin Kim, Jinhwa Lee. Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent. Tetrahedron 2007, 63 (52) , 12845-12852. https://doi.org/10.1016/j.tet.2007.10.056
  10. Tse-Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush. Sodium-Ethanol. 2006,,https://doi.org/10.1002/9780471264194.fos09185
  11. Robert A. Flowers, Edamana Prasad. Chapter 230 Samarium (II) based reductants. 2006,,, 393-473. https://doi.org/10.1016/S0168-1273(06)36004-7
  12. Rita Annunziata, Maurizio Benaglia, Mauro Cinquini, Laura Raimondi. The Effect of Lewis Acids on the Pinacol Homocoupling Reaction of Aldehydes Promoted by Samarium Diiodide. European Journal of Organic Chemistry 1999, 1999 (12) , 3369-3374. https://doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3369::AID-EJOC3369>3.0.CO;2-P
  13. Yoshikazu Iwasawa, Jun Shibata, Katsumasa Nonoshita, Sachie Arai, Hitoshi Masaki, Koji Tomimoto. Stereoselective synthesis of J-104,118 and J-104,123, novel, potent inhibitors of squalene synthase. Tetrahedron 1996, 52 (44) , 13881-13894. https://doi.org/10.1016/0040-4020(96)00850-2
  14. Joseph B. Sweeney. Alkyl Chalcogenides: Oxygen-based Functional Groups. 1995,,, 37-112. https://doi.org/10.1016/B0-08-044705-8/00250-8
  15. . References to Volume 2. 1995,,, 1103-1295. https://doi.org/10.1016/B0-08-044705-8/09010-5
  16. Junji Inanaga, Osamu Ujikawa, Yuichi Handa, Kenji Otsubo, Masaru Yamaguchi. Samarium-mediated acyclic stereoselection in a radical reaction. Journal of Alloys and Compounds 1993, 192 (1-2) , 197-199. https://doi.org/10.1016/0925-8388(93)90229-G
  17. Gilles Courtemanche, Alexandre Alexakis, Jacqueline Vaissermann, Jean-F. Normant. Conjugate addition of organocuprates to γ-methyl-δ-oxy-α,β-enones. Influence of the alkoxy substituent on the diastereoselection. Journal of Organometallic Chemistry 1992, 423 (2) , 281-305. https://doi.org/10.1016/0022-328X(92)83121-W
  18. David J. Ager, Michael B. East. Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 1992, 48 (14) , 2803-2894. https://doi.org/10.1016/S0040-4020(01)90970-6
  19. Andreas Köver, Thilo Schottelius, H. Martin, R. Hoffmann. Diastereoselective route to enantiomerically pure homoallylic pinene alcohols from myrtenyl bromide and aldehydes. Tetrahedron: Asymmetry 1991, 2 (8) , 779-780. https://doi.org/10.1016/S0957-4166(00)80458-9
  20. Y. YAMAMOTO, K. MATSUOKA, H. NEMOTO. ChemInform Abstract: Anti-Cram Selective Reduction of Acyclic Ketones via Electron-Transfer-Initiated Processes.. ChemInform 1988, 19 (42) https://doi.org/10.1002/chin.198842138

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