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

Authors

Sujen Lai, University of New Hampshire
Charles K. Zercher, University of New HampshireFollow
Jerry P. Jasinski, Keene State CollegeFollow
Seth N. Reid, Keene State College
Richard J. Staples, Harvard University

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.

Department

Chemistry

Publication Date

12-1-2001

Journal Title

Organic Letters

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/ol016788n

Document Type

Article

Recommended Citation

Tandem Chain Extension-Aldol Reaction: Syn Selectivity with a Zinc Enolate, Lai, S-J.; Zercher, C. K.; Jasinski, J. P.; Reid, S. N.; Staples, R. J. Org. Lett. 2001, 3, 4169-4171.

Rights

Copyright © 2001, American Chemical Society