4.7 Article

Reversal of Diastereoselectivity in Reactions of the Trifluoroacetaldehyde Ethyl Hemiacetal with Enamines and Imines: Metal-Free, Complementary anti- and syn-Selective Synthesis of 4,4,4-Trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 1, 页码 285-288

出版社

AMER CHEMICAL SOC
DOI: 10.1021/jo101733j

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  1. Japan Society for the Promotion of Science (JSPS) [19550104, 14750665]
  2. Central Glass Co., Ltd.
  3. Grants-in-Aid for Scientific Research [14750665, 19550104] Funding Source: KAKEN

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A complete reversal of diastereoselectivity was observed for reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines, derived from propiophenones, that produce 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1 -butanones. This process serves as the first reliable, metal-free, complementary anti- and syn-selective method to prepare 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones.

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