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

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

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 a...

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Veröffentlicht in:Organic letters 2001-12, Vol.3 (26), p.4169-4171
Hauptverfasser: Lai, Sujen, Zercher, Charles K, Jasinski, Jerry P, Reid, Seth N, Staples, Richard J
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Stereoisomerism
Zinc - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016788n