Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate

Jun Feng Zhao; Teguh Budiono W. Tjan; Teck Peng Loh

doi:10.1016/j.tetlet.2010.06.066

Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate

Jun Feng Zhao, Teguh Budiono W. Tjan, Teck Peng Loh

Nanyang Technological University

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

15 Scopus citations

Abstract

A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.

Original language	English
Pages (from-to)	5649-5652
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.066
State	Published - 2 Oct 2010
Externally published	Yes

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title = "Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate",

abstract = "A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.",

author = "Zhao, {Jun Feng} and Tjan, {Teguh Budiono W.} and Loh, {Teck Peng}",

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AU - Zhao, Jun Feng

AU - Tjan, Teguh Budiono W.

AU - Loh, Teck Peng

PY - 2010/10/2

Y1 - 2010/10/2

N2 - A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.

AB - A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.

UR - http://www.scopus.com/inward/record.url?scp=77957112412&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.06.066

DO - 10.1016/j.tetlet.2010.06.066

M3 - 文章

AN - SCOPUS:77957112412

SN - 0040-4039

VL - 51

SP - 5649

EP - 5652

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate

Abstract

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