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

Branca C. Van Veen; Steven M. Wales; Jonathan Clayden

doi:10.1021/acs.joc.1c00918

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

4 Citations (Scopus)

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 language	English
Pages (from-to)	8538-8543
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	86
Issue number	12
Early online date	8 Jun 2021
DOIs	https://doi.org/10.1021/acs.joc.1c00918
Publication status	Published - 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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Organic & Biological

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@article{98f6124693bf4fe7a035ab1da4fa2bba,

title = "N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate",

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. ",

author = "\{Van Veen\}, \{Branca C.\} and Wales, \{Steven M.\} and Jonathan Clayden",

note = "Funding Information: This work was funded by the EPSRC through Research Grant EP/L018527. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = jun,

day = "18",

doi = "10.1021/acs.joc.1c00918",

language = "English",

volume = "86",

pages = "8538--8543",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate

AU - Van Veen, Branca C.

AU - Wales, Steven M.

AU - Clayden, Jonathan

PY - 2021/6/18

Y1 - 2021/6/18

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85108591182

U2 - 10.1021/acs.joc.1c00918

DO - 10.1021/acs.joc.1c00918

M3 - Article (Academic Journal)

C2 - 34101454

AN - SCOPUS:85108591182

SN - 0022-3263

VL - 86

SP - 8538

EP - 8543

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

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

Abstract

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

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

Abstract

Bibliographical note

Research Groups and Themes

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

Cite this