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

Branca C. Van Veen, Steven M. Wales, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

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.

Original languageEnglish
Number of pages6
JournalJournal of Organic Chemistry
Volume86
Issue number12
DOIs
Publication statusPublished - 18 Jun 2021

Bibliographical note

Funding Information:
This work was funded by the EPSRC through Research Grant EP/L018527.

Publisher Copyright:
© 2021 American Chemical Society.

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