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. 2001 Dec 27;3(26):4169-71.
doi: 10.1021/ol016788n.

Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate

S Lai  1 , C K Zercher, J P Jasinski, S N Reid, R J Staples
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Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate

S Lai et al. Org Lett. .

Abstract

A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-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 beta-keto ester and amide substrates and anti-stereochemistry observed for a beta-keto imide. [reaction: see text]

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