N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate
Branca C. van Veen, Steven M. Wales and Jonathan Clayden*
*School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, U.K., Email: j.claydenbristol.ac.uk
B. C. van Veen, S. M. Wales, J. Clayden, J. Org. Chem., 2021, 86, 8538-8543.
see article for more reactions
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. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts.
see article for more examples