Chemo- and regioselective reductive transposition of allylic alcohol derivatives via iridium or rhodium catalysis

作者: Rylan J. Lundgren , Bryce N. Thomas

DOI: 10.1039/C5CC07993D

关键词: MetalOrganic chemistryRhodiumCatalysisOlefin fiberTransposition (music)DeoxygenationIridiumChemistryRegioselectivity

摘要: We report highly chemo- and regioselective reductive transpositions of methyl carbonates to furnish olefin products with complementary regioselectivity that established Pd-catalysis. These Rh- Ir-catalysed transformations proceed under mild conditions enable selective deoxygenation in the presence functional groups are susceptible reduction by metal hydrides.

参考文章(38)
Josef M. Herrmann, Burkhard König, Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton–McCombie Deoxygenation European Journal of Organic Chemistry. ,vol. 2013, pp. 7017- 7027 ,(2013) , 10.1002/EJOC.201300657
Barrie J. Marsh, David R. Carbery, One-Pot o-Nitrobenzenesulfonylhydrazide (NBSH) Formation−Diimide Alkene Reduction Protocol Journal of Organic Chemistry. ,vol. 74, pp. 3186- 3188 ,(2009) , 10.1021/JO900237Y
Jian-Lin Huang, Xi-Jie Dai, Chao-Jun Li, Iridium-Catalyzed Direct Dehydroxylation of Alcohols European Journal of Organic Chemistry. ,vol. 2013, pp. 6496- 6500 ,(2013) , 10.1002/EJOC.201301293
Arash Jabbari, Erik J. Sorensen, K. N. Houk, Transition states of the retro-ene reactions of allylic diazenes. Organic Letters. ,vol. 8, pp. 3105- 3107 ,(2006) , 10.1021/OL0612049
Anh Chau, Jean-François Paquin, Mark Lautens, Diastereoselective Palladium-Catalyzed Formate Reduction of Allylic Carbonates en Route to Polypropionate Systems The Journal of Organic Chemistry. ,vol. 71, pp. 1924- 1933 ,(2006) , 10.1021/JO052267S
Dexi Yang, Glenn C. Micalizio, Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition. Journal of the American Chemical Society. ,vol. 134, pp. 15237- 15240 ,(2012) , 10.1021/JA306362M
Michael H. Haukaas, George A. O'Doherty, Enantioselective Synthesis of 2-Deoxy- and 2,3-Dideoxyhexoses Organic Letters. ,vol. 4, pp. 1771- 1774 ,(2002) , 10.1021/OL025844X
P. Andrew Evans, John E. Robinson, Kristofer K. Moffett, Regioselective and enantiospecific rhodium-catalyzed allylic amination with N-(arylsulfonyl)anilines. Organic Letters. ,vol. 3, pp. 3269- 3271 ,(2001) , 10.1021/OL016467B
Mark G Charest, Christian D Lerner, Jason D Brubaker, Dionicio R Siegel, Andrew G Myers, A Convergent Enantioselective Route to Structurally Diverse 6-Deoxytetracycline Antibiotics Science. ,vol. 308, pp. 395- 398 ,(2005) , 10.1126/SCIENCE.1109755
Ming Bian, Zhen Wang, Xiaochun Xiong, Yu Sun, Carlo Matera, K. C. Nicolaou, Ang Li, Total Syntheses of Anominine and Tubingensin A Journal of the American Chemical Society. ,vol. 134, pp. 8078- 8081 ,(2012) , 10.1021/JA302765M