Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

Craig D. Campbell; Carmen Concellon; Andrew D. Smith

doi:10.1016/j.tetasy.2011.04.001

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

Craig D. Campbell, Carmen Concellon, Andrew D. Smith

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

Abstract

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	797-811
Number of pages	15
Journal	Tetrahedron: Asymmetry
Volume	22
Issue number	7
DOIs	https://doi.org/10.1016/j.tetasy.2011.04.001
Publication status	Published - 11 Apr 2011

Access to Document

10.1016/j.tetasy.2011.04.001

Cite this

@article{593d6d69ae4549f8a4980984108830f6,

title = "Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes",

abstract = "The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.",

author = "Campbell, {Craig D.} and Carmen Concellon and Smith, {Andrew D.}",

year = "2011",

month = apr,

day = "11",

doi = "10.1016/j.tetasy.2011.04.001",

language = "English",

volume = "22",

pages = "797--811",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "7",

}

TY - JOUR

T1 - Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

AU - Campbell, Craig D.

AU - Concellon, Carmen

AU - Smith, Andrew D.

PY - 2011/4/11

Y1 - 2011/4/11

N2 - The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.

AB - The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetasy.2011.04.001

DO - 10.1016/j.tetasy.2011.04.001

M3 - Article

SN - 0957-4166

VL - 22

SP - 797

EP - 811

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 7

ER -

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

Abstract

Access to Document

Fingerprint

Cite this