A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters

Chao Deng; Li Jia Wang; Jun Zhu; Yong Tang

doi:10.1002/anie.201206376

A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters

Chao Deng, Li Jia Wang, Jun Zhu, Yong Tang

CAS - Shanghai Institute of Organic Chemistry

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

88 Scopus citations

Abstract

Triangulation method: The catalytic enantioselective cyclopropanation of multisubstituted olefins with phenyliodonium ylide malonate has been achieved in the presence of a chiral bisoxazoline copper(I) complex (see scheme). A wide range of substrates undergo the reaction to provide optically active 1,1-cyclopropane diesters in high yield with up to >99 %-ee. A rationale for the enantioselective induction has been proposed.

Original language	English
Pages (from-to)	11620-11623
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	46
DOIs	https://doi.org/10.1002/anie.201206376
State	Published - 12 Nov 2012
Externally published	Yes

Keywords

asymmetric catalysis
carbenes
copper
cyclopropanation
homogeneous catalysis

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10.1002/anie.201206376

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title = "A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters",

abstract = "Triangulation method: The catalytic enantioselective cyclopropanation of multisubstituted olefins with phenyliodonium ylide malonate has been achieved in the presence of a chiral bisoxazoline copper(I) complex (see scheme). A wide range of substrates undergo the reaction to provide optically active 1,1-cyclopropane diesters in high yield with up to >99 \%-ee. A rationale for the enantioselective induction has been proposed.",

keywords = "asymmetric catalysis, carbenes, copper, cyclopropanation, homogeneous catalysis",

author = "Chao Deng and Wang, \{Li Jia\} and Jun Zhu and Yong Tang",

year = "2012",

month = nov,

day = "12",

doi = "10.1002/anie.201206376",

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volume = "51",

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journal = "Angewandte Chemie - International Edition",

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T1 - A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters

AU - Deng, Chao

AU - Wang, Li Jia

AU - Zhu, Jun

AU - Tang, Yong

PY - 2012/11/12

Y1 - 2012/11/12

N2 - Triangulation method: The catalytic enantioselective cyclopropanation of multisubstituted olefins with phenyliodonium ylide malonate has been achieved in the presence of a chiral bisoxazoline copper(I) complex (see scheme). A wide range of substrates undergo the reaction to provide optically active 1,1-cyclopropane diesters in high yield with up to >99 %-ee. A rationale for the enantioselective induction has been proposed.

AB - Triangulation method: The catalytic enantioselective cyclopropanation of multisubstituted olefins with phenyliodonium ylide malonate has been achieved in the presence of a chiral bisoxazoline copper(I) complex (see scheme). A wide range of substrates undergo the reaction to provide optically active 1,1-cyclopropane diesters in high yield with up to >99 %-ee. A rationale for the enantioselective induction has been proposed.

KW - asymmetric catalysis

KW - carbenes

KW - copper

KW - cyclopropanation

KW - homogeneous catalysis

UR - https://www.scopus.com/pages/publications/84868581747

U2 - 10.1002/anie.201206376

DO - 10.1002/anie.201206376

M3 - 文章

C2 - 23065765

AN - SCOPUS:84868581747

SN - 1433-7851

VL - 51

SP - 11620

EP - 11623

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 46

ER -

A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters

Abstract

Keywords

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