Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones

Add time:08/16/2019    Source:sciencedirect.com

Substituted acrylonitrile and ethyl acrylate bearing a masked α-hydroxyaldehyde were easily synthesised by a Barbier type reaction between the monoacetal of glyoxal and bromomethyl acrylonitrile or ethyl bromomethyl acrylate. We prepared these interesting synthons in an enantiomerically pure form by enzymatic resolution with Candida rugosa lipase, or by microbial reduction of the corresponding ketones using Aspergillus niger and Lactobacillus kefir.

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