Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands

被引：6

作者：

Chakka, Sai Kumar ^{[1
]}

Cele, Zamani E. D. ^{[4
]}

Sosibo, Sphelele C. ^{[4
]}

Francis, Vivian ^{[1
]}

Arvidsson, Per I. ^{[2
,3
]}

Kruger, Hendrik G. ^{[1
]}

Maguire, Glenn E. M. ^{[1
]}

Govender, Thavendran ^{[4
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem, Durban, South Africa

[2] Uppsala Univ, Uppsala Biomed Ctr, Dept Med Chem, Uppsala, Sweden

[3] AstraZeneca R&D Sodertalje, CNSP iMed, Innovat Med, S-15185 Sodertalje, Sweden

[4] Univ KwaZulu Natal, Sch Hlth Sci, Durban, South Africa

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 08期

关键词：

MICHAEL ADDITION; ENANTIOSELECTIVE CYANOSILYLATION; ALDOL ADDITIONS; N-OXIDES; THIOLS; ALDEHYDES; CATALYSTS; KETONES;

D O I：

10.1016/j.tetasy.2012.04.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of novel TIQ based N,N'-oxide ligands were synthesised and screened for their catalytic activity in the enantioselective conjugate addition of thioglycolate to chalcones. Bulky groups on the side chain of the TIQ backbone provided the highest enantioselectivity of up to 88% with 10 mol % catalyst loading. It was also observed that these reactions proceeded optimally in the presence of dichloromethane as a solvent. Screening of various metals emphasized La(OTf)(3) as the ideal pre-catalyst for this particular reaction. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：616 / 622

页数：7

共 43 条

[1] Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis [J].