N -Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N -Boc Ethyl Oxamate.

Autor:	van Veen BC; School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K., Wales SM; School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K., Clayden J; School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2021 Jun 18; Vol. 86 (12), pp. 8538-8543. Date of Electronic Publication: 2021 Jun 08.
DOI:	10.1021/acs.joc.1c00918
Abstrakt:	We report the practical, scalable synthesis of a range of N -methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N -Boc ethyl oxamate to deliver the corresponding N -Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N -methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N -methyl allylic amines, many of which have limited commercial availability.
Databáze:	MEDLINE
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