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

Minhui Han, Xiaodong Ma, Shangchu Yao, Yuxuan Ding, Zihan Yan, Adila Adijiang, Yufei Wu, Hengzhao Li, Yuntong Zhang, Peng Lei, Yun Ling and Jie An*

*College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China, Email: jie_ancau.edu.cn

M. Han, X. Ma, S. Yao, Y. Ding, Z. Yan, A. Adijiang, Y. Wu, H. Li, Y. Zhang, P. Lei, Y. Ling, J. An, J. Org. Chem., 2017, 82, 1285-1291.

DOI: 10.1021/acs.joc.6b02950 (free Supporting Information)


Abstract

A modified Bouveault-Blanc reduction enables the synthesis of α,α-dideuterio alcohols from carboxylic acid esters using commercially available sodium dispersions as the electron donor and ethanol-d1 as the deuterium source. This operationally simple reaction results in excellent deuterium incorporation across a broad range of aliphatic esters.

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Key Words

Bouveault-Blanc Reduction


ID: J42-Y2017