In:
RSC Advances, Royal Society of Chemistry (RSC), Vol. 13, No. 20 ( 2023), p. 13511-13515
Abstract:
α,β-Unsaturated esters are key structural motifs widely distributed in various biologically active molecules, and their Z / E -stereoselective synthesis has always been considered highly attractive in organic synthesis. Herein, we present a 〉 99% ( E )-stereoselective one-pot synthetic approach towards β-phosphoroxylated α,β-unsaturated esters via a mild trimethylamine-catalyzed 1,3-hydrogen migration of the corresponding unconjugated intermediates derived from the solvent-free Perkow reaction between low-cost 4-chloroacetoacetates and phosphites. Versatile β,β-disubstituted ( E )-α,β-unsaturated esters were thus afforded with full ( E )-stereoretentivity by cleavage of the phosphoenol linkage via Negishi cross-coupling. Moreover, a stereoretentive ( E )-rich mixture of a α,β-unsaturated ester derived from 2-chloroacetoacetate was obtained and both isomers were easily afforded in one operation.
Type of Medium:
Online Resource
ISSN:
2046-2069
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2023
detail.hit.zdb_id:
2623224-8
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