l-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone

Xiao Ying Xu, Yan Zhao Wang, Lin Feng Cun, Liu Zhu Gong

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Direct aldol reactions of aldehydes with methylthio- and fluoroacetone catalyzed by proline amides have been investigated. l-Prolinamide 5e was found to be the best catalyst. Under the optimized reaction conditions, a series of aromatic and aliphatic aldehydes reacted smoothly with methylthioacetone, to generate 1-methylthio-4-hydroxyketones 3 in good yields and with high regio- and enantioselectivities. Excellent enantioselectivities of up to 98% ee were observed for aromatic aldehydes and even higher enantioselectivities of >99% ee were observed for aliphatic aldehydes. Asymmetric direct aldol reactions of fluoroacetone with aldehydes in the presence of 20 mol % of 5e preferentially occurred at the fluoromethyl group, yielding products with high enantioselectivities (up to 98% ee).

Original languageEnglish (US)
Pages (from-to)237-242
Number of pages6
JournalTetrahedron Asymmetry
Volume18
Issue number2
DOIs
StatePublished - Feb 14 2007

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