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Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters

✍ Scribed by Shigeki Sano; Katsuyuki Saito; Yoshimitsu Nagao

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 137 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00778-0

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✦ Synopsis

A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH 4 in EtOH was developed. The one-pot reaction gave a-fluoro-a,b-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed.

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