Issue 29, 2014

High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction

Abstract

A general process for the high-yielding synthesis of substituted chiral and achiral α-substituted acrylates was achieved through the sequential one-pot combination of a metal-free reductive coupling reaction followed by an Eschenmoser methylenation. The proline catalyzed reaction of Meldrum's acid, aldehydes and Hantzsch ester followed by methylenation was successful with Eschenmoser's salt in the presence of an alcohol solvent. Herein, we have shown the high-yielding synthesis of privileged building blocks from chiral/achiral α-substituted acrylates and shown them to be very good intermediates in the pharmaceuticals and natural products synthesis.

Graphical abstract: High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction

Supplementary files

Article information

Article type
Paper
Submitted
29 Mar 2014
Accepted
30 May 2014
First published
30 May 2014

Org. Biomol. Chem., 2014,12, 5400-5406

Author version available

High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction

D. B. Ramachary, C. Venkaiah and Y. V. Reddy, Org. Biomol. Chem., 2014, 12, 5400 DOI: 10.1039/C4OB00667D

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