Journal article
N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate
Journal of Organic Chemistry, Vol.86(12), pp.8538-8543
2021
PMID: 34101454
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.
Details
- Title
- N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate
- Authors
- Branca C. van Veen (Author) - University of BristolSteven M. Wales (Author) - University of BristolJonathan Clayden (Corresponding Author) - University of Bristol
- Publication details
- Journal of Organic Chemistry, Vol.86(12), pp.8538-8543
- Publisher
- American Chemical Society
- DOI
- 10.1021/acs.joc.1c00918
- ISSN
- 1520-6904
- PMID
- 34101454
- Grant note
- EP/L018527 / EPSRC; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC)
- Organisation Unit
- Student Services and Engagement; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99707483902621
- Output Type
- Journal article
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- Chemistry, Organic
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