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

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10.1016/j.tetasy.2011.04.001

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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.\}",

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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.

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DO - 10.1016/j.tetasy.2011.04.001

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Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

Abstract

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