Diastereoselective aldol reactions of enolates generated from vicinally substituted trimethylsilylmethyl cyclopropyl ketones

Yadav, Veejendra K. ; Balamurugan, Rengarajan (2003) Diastereoselective aldol reactions of enolates generated from vicinally substituted trimethylsilylmethyl cyclopropyl ketones Organic Letters, 5 (23). pp. 4281-4284. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol035481g

Related URL: http://dx.doi.org/10.1021/ol035481g

Abstract

Vicinally substituted trimethylsilylmethyl cyclopropyl ketones undergo facile desilylative ring opening with Lewis acids under mild conditions. The enolates, thus generated, undergo aldol addition with aldehydes and ketones. The diastereoselectivity of the reaction with aldehydes depends on the nature of the Lewis acid used. The resulting aldol product is easily converted into a substituted tetrahydrofuran derivative.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:58219
Deposited On:31 Aug 2011 06:55
Last Modified:31 Aug 2011 06:55

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