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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:

B. C. van Veen, S. M. Wales, J. Clayden, J. Org. Chem., 2021, 86, 8538-8543.

DOI: 10.1021/acs.joc.1c00918

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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.

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Key Words

Mitsunobu reaction, allylic amines, tert-butyl carbamates

ID: J42-Y2021