Catalytic asymmetric carbon-carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands

被引：14
作者：
Cele, Zamani E. D. [1 ]
Sosibo, Sphelele C. [1 ]
Andersson, Pher G. [1 ,2 ]
Kruger, Hendrik G. [1 ]
Maguire, Glenn E. M. [1 ]
Govender, Thavendran [1 ]
机构：
[1] Univ KwaZulu Natal, Sch Hlth Sci, Catalysis & Peptide Res Unit, Durban, South Africa
[2] Uppsala Univ, Dept Biochem & Organ Chem, SE-75123 Uppsala, Sweden
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 04期
关键词：
DIELS-ALDER REACTION; ENANTIOSELECTIVE MICHAEL ADDITION; CYCLIC 1,3-DICARBONYL COMPOUNDS; HETERO-ENE REACTIONS; CONJUGATE ADDITION; ALPHA-KETOESTERS; ALDEHYDES; KETONES; ORGANOCATALYSTS; THIOGLYCOLATE;
D O I：
10.1016/j.tetasy.2013.01.004
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The use of TIQ-N,N'-dioxide ligands in asymmetric C-C bond forming reactions is described. In the Michael addition of cyclohexane-1,3-dione and malonates to beta,gamma-unsaturated alpha-ketoesters, excellent yields (up to 93%) and moderate to good enantioselectivities (70-89% ee) were obtained. The catalytic hetero-ene reaction of 2-methoxypropene with phenylglyoxal gave the ene product in excellent yield (95%) with moderate enantioselectivity (77% ee). The catalyst system performed well at temperatures ranging from 0 to 30 degrees C and relatively low catalyst loading (0.2-5 mol %) with dichloromethane being the preferred solvent for all reactions. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：191 / 195
页数：5
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