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