Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives

Feng Xu; Richard D. Tillyer; David M. Tschaen; Edward J.J. Grabowski; Paul J. Reider

doi:10.1016/S0957-4166(98)00157-8

Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives

Feng Xu, Richard D. Tillyer, David M. Tschaen, Edward J.J. Grabowski, Paul J. Reider

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

52 Scopus citations

Abstract

Reaction of t-BuLi with a mixture of aryl bromide and chiral diamine, amino ether or diether, in toluene at -78°C provided chiral aryllithium complexes efficiently. Reaction of these aryllithium complexes with α,β- unsaturated tert-butyl esters afforded the 1,4-addition products in up to 88% ee.

Original language	English (US)
Pages (from-to)	1651-1655
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	9
Issue number	10
DOIs	https://doi.org/10.1016/S0957-4166(98)00157-8
State	Published - May 22 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(98)00157-8

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title = "Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives",

abstract = "Reaction of t-BuLi with a mixture of aryl bromide and chiral diamine, amino ether or diether, in toluene at -78°C provided chiral aryllithium complexes efficiently. Reaction of these aryllithium complexes with α,β- unsaturated tert-butyl esters afforded the 1,4-addition products in up to 88% ee.",

author = "Feng Xu and Tillyer, {Richard D.} and Tschaen, {David M.} and Grabowski, {Edward J.J.} and Reider, {Paul J.}",

year = "1998",

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T1 - Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives

AU - Xu, Feng

AU - Tillyer, Richard D.

AU - Tschaen, David M.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 1998/5/22

Y1 - 1998/5/22

N2 - Reaction of t-BuLi with a mixture of aryl bromide and chiral diamine, amino ether or diether, in toluene at -78°C provided chiral aryllithium complexes efficiently. Reaction of these aryllithium complexes with α,β- unsaturated tert-butyl esters afforded the 1,4-addition products in up to 88% ee.

AB - Reaction of t-BuLi with a mixture of aryl bromide and chiral diamine, amino ether or diether, in toluene at -78°C provided chiral aryllithium complexes efficiently. Reaction of these aryllithium complexes with α,β- unsaturated tert-butyl esters afforded the 1,4-addition products in up to 88% ee.

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U2 - 10.1016/S0957-4166(98)00157-8

DO - 10.1016/S0957-4166(98)00157-8

M3 - Article

AN - SCOPUS:0032557499

SN - 0957-4166

VL - 9

SP - 1651

EP - 1655

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 10

ER -

Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives

Abstract

All Science Journal Classification (ASJC) codes

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