Photoredox α-vinylation of α-amino acids and N -aryl amines

Adam Noble; David W.C. MacMillan

doi:10.1021/ja506094d

Photoredox α-vinylation of α-amino acids and N -aryl amines

Adam Noble, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

358 Scopus citations

Abstract

A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

Original language	English (US)
Pages (from-to)	11602-11605
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	33
DOIs	https://doi.org/10.1021/ja506094d
State	Published - Aug 20 2014

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

Access to Document

10.1021/ja506094d

Cite this

@article{5eedbd86902145d6a5decfd3e63668a3,

title = "Photoredox α-vinylation of α-amino acids and N -aryl amines",

abstract = "A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.",

author = "Adam Noble and MacMillan, {David W.C.}",

year = "2014",

month = aug,

day = "20",

doi = "10.1021/ja506094d",

language = "English (US)",

volume = "136",

pages = "11602--11605",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "33",

}

TY - JOUR

T1 - Photoredox α-vinylation of α-amino acids and N -aryl amines

AU - Noble, Adam

AU - MacMillan, David W.C.

PY - 2014/8/20

Y1 - 2014/8/20

N2 - A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

AB - A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

UR - http://www.scopus.com/inward/record.url?scp=84906334075&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906334075&partnerID=8YFLogxK

U2 - 10.1021/ja506094d

DO - 10.1021/ja506094d

M3 - Article

C2 - 25026314

AN - SCOPUS:84906334075

SN - 0002-7863

VL - 136

SP - 11602

EP - 11605

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 33

ER -

Photoredox α-vinylation of α-amino acids and N -aryl amines

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this