Title

Tandem Chain Extension-Aldol Reaction: Syn Selectivity with a Zinc Enolate

Abstract

A tandem chain extension−aldol reaction was developed in which β-keto esters are transformed to α-substituted-γ-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for β-keto ester and amide substrates and anti-stereochemistry observed for a β-keto imide.

Publication Date

12-1-2001

Journal Title

Organic Letters

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/ol016788n

Document Type

Article

Rights

Copyright © 2001, American Chemical Society