Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

Jiajing Tan; Cheol Hong Cheon; Hisashi Yamamoto

doi:10.1002/anie.201203092

Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

Jiajing Tan, Cheol Hong Cheon, Hisashi Yamamoto

Department of Chemistry

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

47 Citations (Scopus)

Abstract

A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.

Original language	English
Pages (from-to)	8264-8267
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	33
DOIs	https://doi.org/10.1002/anie.201203092
Publication status	Published - 2012 Aug 13

Keywords

BOX ligands
Claisen rearrangement
asymmetric catalysis
copper
quaternary carbon centers

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201203092

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abstract = "A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.",

keywords = "BOX ligands, Claisen rearrangement, asymmetric catalysis, copper, quaternary carbon centers",

author = "Jiajing Tan and Cheon, {Cheol Hong} and Hisashi Yamamoto",

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AU - Tan, Jiajing

AU - Cheon, Cheol Hong

AU - Yamamoto, Hisashi

PY - 2012/8/13

Y1 - 2012/8/13

N2 - A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.

AB - A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.

KW - BOX ligands

KW - Claisen rearrangement

KW - asymmetric catalysis

KW - copper

KW - quaternary carbon centers

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DO - 10.1002/anie.201203092

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 33

ER -

Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

Abstract

Keywords

ASJC Scopus subject areas

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