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Highly Enantioselective Organocatalyzed Construction of Quaternary Carbon Centers via Cross-Aldol Reaction of Ketones in Water

✍ Scribed by Changwu Zheng; Yongyong Wu; Xiaosheng Wang; Gang Zhao

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 229 KB
Volume: 350
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200800248

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✦ Synopsis

Abstract

The asymmetric construction of quaternary carbon centers via cross‐aldol reactions of ketones with β,γ‐unsaturated keto esters catalyzed by 4‐(tert‐butyldiphenylsilyloxy)‐pyrrolidine‐2‐carboxylic acid in water is described. The adducts bearing two adjacent chiral centers were obtained in high yields, mostly up to 99% ee, and with high diastereoselectivities. The corresponding polyfunctional products could also be easily transformed to useful lactones with three chiral centers.

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