Asymmetric Nucleophilic Acylation of Aldehydes via 1, 1??Heterodisubstituted Alkenes

H Monenschein, G Dräger, A Jung…

Index: Monenschein, Holger; Draeger, Gerald; Jung, Alexander; Kirschning, Andreas Chemistry - A European Journal, 1999 , vol. 5, # 8 p. 2270 - 2280

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Citation Number: 36

Abstract

Abstract Aldehydescanbe efficiently acetylated in an asymmetric manner via 1, 1- heterodisubstituted alkenes. The method combines a homologation step of the starting aldehyde 1 followed by the Sharpless asymmetric dihydroxylation of intermediate prochiral 1, 1-heterodisubstituted alkenes 2. The sequence works particularly well with ketene O, O- acetals as intermediates and allows the synthesis of α-hydroxy carboxylates 3 in high ...

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