Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and 
α-Unsubstituted Aldehydes

List, Benjamin; Pojarliev, Peter; Castello, Chris

doi:10.1021/ol006976y

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Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and α-Unsubstituted Aldehydes

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List, B., Pojarliev, P., & Castello, C. (2001). Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and α-Unsubstituted Aldehydes. Organic Letters, 3(4), 573-575. doi:10.1021/ol006976y.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A4DB-C

Abstract

With this communication we extend the methodology of proline-catalyzed direct asymmetric aldol reactions to include α-unsubstituted aldehydes as acceptors. This important aldehyde class gives the corresponding aldols in 22−77% yield and up to 95% ee when the reactions are performed in pure acetone or in ketone/chloroform mixtures. On the basis of these results we have developed a concise new synthesis of (S)-ipsenol.