Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects

SE Denmark, RA Stavenger, KT Wong…

Index: Denmark, Scott E.; Stavenger, Robert A.; Wong, Ken-Tsung; Su, Xiping Journal of the American Chemical Society, 1999 ,  vol. 121,  # 21  p. 4982 - 4991

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Citation Number: 115

Abstract

Trichlorosilyl enolates of ketones (enoxytrichlorosilanes) were demonstrated to be highly reactive aldol addition reagents. Trichlorosilyl enolates of cyclohexanone (E-enolate) and propiophenone (Z-enolate) reacted readily at room temperature with a wide variety of aldehydes to afford aldol addition products in high yield and diastereoselectivity (E→ syn, Z→ anti). These reactions were shown to be highly susceptible to acceleration by catalytic ...