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Carboxylation and Mitsunobu reaction of amines to give carbamates: retention vs inversion of configuration is substituent-dependent.

作者信息

Dinsmore Christopher J, Mercer Swati P

机构信息

Department of Medicinal Chemistry, Merck Research Laboratories, West Point, Pennsylvania 19486, USA.

出版信息

Org Lett. 2004 Aug 19;6(17):2885-8. doi: 10.1021/ol0491080.

DOI:10.1021/ol0491080
PMID:15330639
Abstract

A mild method for the synthesis of carbamates from amino alcohols involves sequential carboxylation with carbon dioxide, followed by a Mitsunobu reaction. Unexpectedly, the stereochemical course of the Mitsunobu reaction is dependent on whether the carbamic acid intermediate is N-substituted with hydrogen (retention) or carbon (inversion).

摘要

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