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J Org Chem. 2017 Jan 20;82(2):1285-1290. doi: 10.1021/acs.joc.6b02950. Epub 2017 Jan 9.

Development of a Modified Bouveault-Blanc Reduction for the Selective Synthesis of α,α-Dideuterio Alcohols.

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1
College of Science, China Agricultural University , No. 2 Yuanmingyuan West Road, Beijing 100193, China.

Abstract

A modified Bouveault-Blanc reduction has been developed for the synthesis of α,α-dideuterio alcohols from carboxylic acid esters. Sodium dispersions are used as the electron donor in this electron transfer reaction, and ethanol-d1 is employed as the deuterium source. This reaction uses stable, cheap, and commercially available reagents, is operationally simple, and results in excellent deuterium incorporation across a broad range of aliphatic esters, which provides an attractive alternative to reactions mediated by expensive pyrophoric alkali metal deuterides.

PMID:
28029787
DOI:
10.1021/acs.joc.6b02950

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