Carboxylation and Mitsunobu reaction of amines to give carbamates: retention vs inversion of configuration is substituent-dependent |
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Authors: | Dinsmore Christopher J Mercer Swati P |
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Institution: | Department of Medicinal Chemistry, Merck Research Laboratories, West Point, Pennsylvania 19486, USA. christopher_dinsmore@merck.com |
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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). |
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