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

The Journal of Organic Chemistry
Branca C van VeenJonathan Clayden

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.

References

Jun 1, 1967·The Journal of Organic Chemistry·H Kaufmann, D K Fukushima
Feb 19, 2002·Chemical Reviews·Mogens Johannsen, Karl Anker Jørgensen
Jul 9, 2009·Journal of the American Chemical Society·Barbara WeinerBen L Feringa
Apr 7, 2012·Journal of the American Chemical Society·Julien LefrancJonathan Clayden
Apr 24, 2016·Chemistry : a European Journal·Manjeet K MajhailMichael C Willis
Jul 19, 2016·Chemical Communications : Chem Comm·James D FirthAdam Nelson
Jan 3, 2019·Angewandte Chemie·Hossay AbasJonathan Clayden
Feb 5, 2019·Journal of the American Chemical Society·Honghui Lei, Tomislav Rovis
Jul 6, 2019·Journal of the American Chemical Society·Samir GhoraiChangkun Li
Oct 2, 2020·Journal of the American Chemical Society·Qiang ChengTobias Ritter

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