Bottom-Up Synthesis of Supported Thioureas and Their Use in Enantioselective Solvent-Free Aza-Henry and Michael Additions

被引：24
|
作者：
Andres, Jose M. [1 ,2 ]
de La Cruz, Noelia [1 ,2 ]
Valle, Maria [1 ,2 ]
Pedrosa, Rafael [1 ,2 ]
机构：
[1] Univ Valladolid, Fac Ciencias, Inst CINQUIMA, Paseo Belen 7, E-47011 Valladolid, Spain
[2] Univ Valladolid, Fac Ciencias, Dept Quim Organ, Paseo Belen 7, E-47011 Valladolid, Spain
来源：
CHEMPLUSCHEM | 2016年 / 81卷 / 01期
关键词：
enantioselectivity; Michael addition; organocatalysis; supported catalysts; thioureas; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; STEREOCONTROLLED CONSTRUCTION; BIFUNCTIONAL ORGANOCATALYSTS; CHIRAL ORGANOCATALYSTS; TERTIARY STEREOCENTERS; ASYMMETRIC ADDITION; ADJACENT QUATERNARY; MESOPOROUS SILICA; ALDOL REACTION;
D O I：
10.1002/cplu.201500476
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two sets of supported chiral thioureas, which differ in the length of the tether that connects the chiral appendage to the polymer structure and the effective functionalization, have been prepared by copolymerization of styrene, novel styryl thioureas derived from l-valine, and divinylbenzene. The efficiency of these polymeric thioureas has been tested in two different enantioselective transformations, namely, aza-Henry and nitro-Michael reactions, in neat reaction conditions. The obtained results show that it is possible to recycle the thiourea, and they are able to promote the reactions with good enantioselectivity at a low catalyst loading.
引用
收藏
页码：86 / 92
页数：7
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