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Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene

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    Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1991, 56, 22, 6440–6447
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    https://doi.org/10.1021/jo00022a041
    Published October 1, 1991
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    This article is cited by 50 publications.

    1. Huw M. L. Davies. Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C–H Functionalization. The Journal of Organic Chemistry 2019, 84 (20) , 12722-12745. https://doi.org/10.1021/acs.joc.9b02428
    2. Albert Padwa and Yan Zou . Solvent and Ligand Effects Associated with the Rh(II)-Catalyzed Reactions of α-Diazo-Substituted Amido Esters. The Journal of Organic Chemistry 2015, 80 (3) , 1802-1808. https://doi.org/10.1021/jo502725d
    3. Young-Sun Do, Ruiying Sun, Hee Jin Kim, Jung Eun Yeo, Sung-Hee Bae and Sangho Koo . Ring-Expansion Protocol: Preparation of Synthetically Versatile Dihydrotropones. The Journal of Organic Chemistry 2009, 74 (2) , 917-920. https://doi.org/10.1021/jo802064c
    4. Jeremy P. Olson and, Huw M. L. Davies. Asymmetric [4 + 3] Cycloadditions between Benzofuranyldiazoacetates and Dienes:  Formal Synthesis of (+)-Frondosin B. Organic Letters 2008, 10 (4) , 573-576. https://doi.org/10.1021/ol702844g
    5. Huw M. L. Davies,, Michael G. Coleman, and, Dominic L. Ventura. Balance between Allylic C−H Activation and Cyclopropanation in the Reactions of Donor/Acceptor-Substituted Rhodium Carbenoids with trans-Alkenes. Organic Letters 2007, 9 (24) , 4971-4974. https://doi.org/10.1021/ol702218w
    6. Huw M. L. Davies,, Øystein Loe, and, Douglas G. Stafford. Sequential Cycloaddition Approach to the Tricyclic Core of Vibsanin E. Total Synthesis of (±)-5-epi-10-epi-Vibsanin E. Organic Letters 2005, 7 (25) , 5561-5563. https://doi.org/10.1021/ol052005c
    7. Huw M. L. Davies and, Qihui Jin. Double C−H Activation Strategy for the Asymmetric Synthesis of C2-Symmetric Anilines. Organic Letters 2004, 6 (11) , 1769-1772. https://doi.org/10.1021/ol0495467
    8. Huw M. L. Davies and, L. Mark Hodges. Rhodium Carboxylate Catalyzed Decomposition of Vinyldiazoacetates in the Presence of Heterodienes:  Enantioselective Synthesis of the 6-Azabicyclo[3.2.2]nonane and 6-Azabicyclo[3.2.2]nonanone Ring Systems. The Journal of Organic Chemistry 2002, 67 (16) , 5683-5689. https://doi.org/10.1021/jo025697g
    9. Huw M. L. Davies,, Rebecca L. Calvo,, Robert J. Townsend,, Pingda Ren, and, R. Melvyn Churchill. An Exploratory Study of Type II [3 + 4] Cycloadditions between Vinylcarbenoids and Dienes. The Journal of Organic Chemistry 2000, 65 (14) , 4261-4268. https://doi.org/10.1021/jo991959b
    10. Huw M. L. Davies and, Brian D. Doan. Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement Sequence. The Journal of Organic Chemistry 1999, 64 (23) , 8501-8508. https://doi.org/10.1021/jo990888d
    11. Huw M. L. Davies,, Gulzar Ahmed,, Rebecca L. Calvo,, Melvyn Rowen Churchill, and, David G. Churchill. Asymmetric Synthesis of 2,3-Dihydrofurans by Reaction of Rhodium-Stabilized Vinylcarbenoids with Vinyl Ethers. The Journal of Organic Chemistry 1998, 63 (8) , 2641-2645. https://doi.org/10.1021/jo972189b
    12. Huw M. L. Davies,, Gulzar Ahmed, and, Melvyn Rowen Churchill. Asymmetric Synthesis of Highly Functionalized 8-Oxabicyclo[3.2.1]octene Derivatives. Journal of the American Chemical Society 1996, 118 (44) , 10774-10782. https://doi.org/10.1021/ja962081y
    13. Ming Bao, Su Zhou, Xinfang Xu. Synthesis of N ‐Heterocycles via [3 + n] Cycloaddition Reactions of Vinyl Metal Carbene Intermediates. 2022, 213-238. https://doi.org/10.1002/9781119757153.ch5
    14. Bingyang Wang, Bo Xu, Wen Xun, Yiming Guo, Jing Zhang, Fayang G. Qiu. A General Strategy for the Construction of Calyciphylline A‐Type Alkaloids: Divergent Total Syntheses of (−)‐Daphenylline and (−)‐Himalensine A. Angewandte Chemie 2021, 133 (17) , 9525-9529. https://doi.org/10.1002/ange.202016212
    15. Bingyang Wang, Bo Xu, Wen Xun, Yiming Guo, Jing Zhang, Fayang G. Qiu. A General Strategy for the Construction of Calyciphylline A‐Type Alkaloids: Divergent Total Syntheses of (−)‐Daphenylline and (−)‐Himalensine A. Angewandte Chemie International Edition 2021, 60 (17) , 9439-9443. https://doi.org/10.1002/anie.202016212
    16. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium( II ) carboxylates. 2017https://doi.org/10.1002/9780471264194.fos08768.pub6
    17. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium( II ) carboxylates. 2017https://doi.org/10.1002/9780471264194.fos08768.pub7
    18. Na Liu, Wangze Song, Casi M. Schienebeck, Min Zhang, Weiping Tang. Synthesis of naturally occurring tropones and tropolones. Tetrahedron 2014, 70 (49) , 9281-9305. https://doi.org/10.1016/j.tet.2014.07.065
    19. J.L. Mascareñas, M. Gulías, F. López. 5.13 (4+3) Cycloadditions. 2014, 595-655. https://doi.org/10.1016/B978-0-08-097742-3.00514-0
    20. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium ( II ) Carboxylates. 2013, 419-425. https://doi.org/10.1002/9780471264194.fos08768.pub5
    21. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium ( II ) Carboxylates. 2011, 488-492. https://doi.org/10.1002/9780471264194.fos08768.pub4
    22. Etienne Nadeau, Huw M. L. Davies. Methyl ( E )-4-Phenyl-2-diazo-3-butenoate. 2011https://doi.org/10.1002/047084289X.rn01317
    23. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium( II ) carboxylates. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos08768.pub3
    24. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium( II ) carboxylates. 2009, 000-000. https://doi.org/10.1002/9780471264194.fos08768.pub2
    25. James R. Manning, Huw M. L. Davies. Methyl 2-Diazo-3-butenoate. 2008https://doi.org/10.1002/047084289X.rn00898
    26. Ángel M. Montaña, Juan A. Barcia, Gabriele Kociok‐Köhn, Mercè Font‐Bardia, Xavier Solans. Synthesis of 3‐Aminotropones from N ‐Boc‐Protected Furan‐2‐amine (= tert ‐Butyl Furan‐2‐ylcarbamate; Boc=( tert ‐Butoxy)carbonyl) by Cycloaddition Reactions and Subsequent Rearrangement. Helvetica Chimica Acta 2008, 91 (2) , 187-208. https://doi.org/10.1002/hlca.200890024
    27. M. Carmen Carreño, Montserrat Ortega‐Guerra, María Ribagorda, M. Jesús Sanz‐Cuesta. Synthesis of 4‐Aminotropones from [(Sulfinyl or Sulfonyl)methyl]‐Substituted p ‐Quinamines. Chemistry – A European Journal 2008, 14 (2) , 621-636. https://doi.org/10.1002/chem.200700940
    28. Valentine G. Nenajdenko, Arkady L. Krasovskiy, Elizabeth S. Balenkova. The chemistry of sulfinyl and sulfonyl enones. Tetrahedron 2007, 63 (51) , 12481-12539. https://doi.org/10.1016/j.tet.2007.10.018
    29. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Rhodium( II ) carboxylates. 2006https://doi.org/10.1002/9780471264194.fos08768
    30. Olcay Anaç, F. Şeyma Güngör, Gökçe Merey. Synthesis of Highly Functionalized γ ‐Lactones via 1,5‐Electrocyclic Ring Closure. Helvetica Chimica Acta 2006, 89 (6) , 1231-1240. https://doi.org/10.1002/hlca.200690120
    31. Ángel M. Montaña, Juan A. Barcia. New synthetic methodology for 3-aminotropones. Tetrahedron Letters 2005, 46 (49) , 8475-8478. https://doi.org/10.1016/j.tetlet.2005.10.021
    32. Wei-Jie Zhao, Ming Yan, Dan Huang, Shun-Jun Ji. New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes. Tetrahedron 2005, 61 (23) , 5585-5593. https://doi.org/10.1016/j.tet.2005.03.093
    33. M. Carmen Carreño, M. Jesús Sanz-Cuesta, María Ribagorda. Ring expansion of sulfur substituted p-quinamines: regiospecific synthesis of 4-aminotropones. Chem. Commun. 2005, vol. 5/2c (8) , 1007-1009. https://doi.org/10.1039/B414666B
    34. Ming Yan, Wei-Jie Zhao, Dan Huang, Shun-Jun Ji. Unusual reaction of aryldiazoacetates with enamines: highly effective synthesis of γ-ketoesters. Tetrahedron Letters 2004, 45 (33) , 6365-6367. https://doi.org/10.1016/j.tetlet.2004.06.086
    35. Yi-Lun Lin, Edward Turos. Rhodium-catalyzed cyclopropanations of allylsilanes and allylstannanes: the role of the silyl/stannyl group in trans–cis stereoselection. Journal of Organometallic Chemistry 2001, 630 (1) , 57-66. https://doi.org/10.1016/S0022-328X(01)00938-X
    36. Huw M. L. Davies, Evan G. Antoulinakis. Intermolecular Metal‐Catalyzed Carbenoid Cyclopropanations. 2001, 1-326. https://doi.org/10.1002/0471264180.or057.01
    37. Huw M.L. Davies, Stephen A. Panaro. Effect of Rhodium Carbenoid Structure on Cyclopropanation Chemoselectivity. Tetrahedron 2000, 56 (28) , 4871-4880. https://doi.org/10.1016/S0040-4020(00)00202-7
    38. Huw M. L. Davies. Dirhodium Tetra(N-arylsulfonylprolinates) as Chiral Catalysts For Asymmetric Transformations of Vinyl- and Aryldiazoacetates. European Journal of Organic Chemistry 1999, 1999 (10) , 2459-2469. https://doi.org/10.1002/(SICI)1099-0690(199910)1999:10<2459::AID-EJOC2459>3.0.CO;2-R
    39. Huw M.L. Davies. [3+4] annulation between rhodium-stabilized vinylcarbenoids and dienes. 1999, 119-164. https://doi.org/10.1016/S1052-2077(99)80006-7
    40. Elizabeth A. Lund, Isaac A. Kennedy, Alex G. Fallis. Dihydrofurans from α-diazoketones due to facile ring opening – cyclization of donor–acceptor cyclopropane intermediates. Canadian Journal of Chemistry 1996, 74 (12) , 2401-2412. https://doi.org/10.1139/v96-269
    41. Herbert Meier, Dieter Gröschl. Reaction of 2H-1-benzothiete with diazo compounds in the presence of rhodium(II) acetate. Tetrahedron Letters 1995, 36 (34) , 6047-6050. https://doi.org/10.1016/0040-4039(95)01239-E
    42. Michael P. Doyle. Transition Metal Carbene Complexes: Cyclopropanation. 1995, 387-420. https://doi.org/10.1016/B978-008046519-7.00116-7
    43. Albert Padwa, David J. Austin. Ligand Effects on the Chemoselectivity of Transition Metal Catalyzed Reactions of α‐Diazo Carbonyl Compounds. Angewandte Chemie International Edition in English 1994, 33 (18) , 1797-1815. https://doi.org/10.1002/anie.199417971
    44. Albert Padwa, David J. Austin. Übergangsmetallkatalysierte Reaktionen von α‐Diazocarbonylverbindungen – Einfluß der Liganden auf die Chemoselektivität. Angewandte Chemie 1994, 106 (18) , 1881-1899. https://doi.org/10.1002/ange.19941061804
    45. Huw M.L. Davies, T. Jeffrey Clark. Synthesis of highly functionalized tropolones by rhodium(II)-catalyzed reactions of vinyldiazomethanes with oxygenated dienes. Tetrahedron 1994, 50 (33) , 9883-9892. https://doi.org/10.1016/S0040-4020(01)89604-6
    46. Elizabeth A. Lund, Isaac A. Kennedy, Alex G. Fallis. Dihydrofurans from α-diazoketones: Facile rearrangement of donor-acceptor cyclopropanes. Tetrahedron Letters 1993, 34 (43) , 6841-6844. https://doi.org/10.1016/S0040-4039(00)91809-4
    47. Louis S. Hegedus. Transition metals in organic synthesis. Annual Survey covering the year 1991. Journal of Organometallic Chemistry 1993, 457 (1-2) , 167-272. https://doi.org/10.1016/0022-328X(93)80496-X
    48. Geoffrey G. Cox, Christopher J. Moody, David J. Austin, Albert Padwa. Chemoselectivity of rhodium carbenoids. A comparison of the selectivity for OH insertion reactions or carbonyl ylide formation versus aliphatic and aromatic CH insertion and cyclopropanation. Tetrahedron 1993, 49 (23) , 5109-5126. https://doi.org/10.1016/S0040-4020(01)81876-7
    49. Huw M.L. Davies. Tandem cyclopropanation/cope rearrangement: a general method for the construction of seven-membered rings. Tetrahedron 1993, 49 (24) , 5203-5223. https://doi.org/10.1016/S0040-4020(01)82371-1
    50. H. M. L. DAVIES, T. J. CLARK, G. F. KIMMER. ChemInform Abstract: Versatile Synthesis of Tropones by Reaction of Rhodium(II)‐Stabilized Vinylcarbenoids with 1‐Methoxy‐1‐((trimethylsilyl)oxy)buta‐1,3‐diene.. ChemInform 1992, 23 (17) https://doi.org/10.1002/chin.199217112
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    Cite this: J. Org. Chem. 1991, 56, 22, 6440–6447
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00022a041
    Published October 1, 1991
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