Highly enantioselective synthesis of syn- and anti-propionate aldols without diastereoselection in the chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal derived from ethyl 2-(methylthio)propionate |
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| Institution: | 1. State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, Kunming 650091, PR China;2. Department of Pharmaceutical Analysis, China Pharmaceutical University, Nanjing 210009, PR China |
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| Abstract: | A mixture of syn- and anti-aldol products containing an α-methylthio group were obtained in good yields with high enantioselectivities in the chiral oxazaborolidinone-promoted aldol reactions of a novel silyl ketene acetal, derived from ethyl 2-(methylthio)propionate, with aldehydes. Subsequent desulfurization resulted in an effective preparation of essentially enantiopure syn- and anti-propionate aldols which were separable. |
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