Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

被引：36
|
作者：
Shubina, Tatyana E. [1 ,2 ]
Freund, Matthias [3 ]
Schenker, Sebastian [3 ]
Clark, Timothy [1 ,2 ]
Tsogoeva, Svetlana B. [3 ]
机构：
[1] Univ Erlangen Nurnberg, Comp Chem Ctr, D-91052 Erlangen, Germany
[2] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat, D-91052 Erlangen, Germany
[3] Univ Erlangen Nurnberg, Dept Chem & Pharm, Chair Organ Chem 1, D-91054 Erlangen, Germany
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷
关键词：
bifunctional organocatalyst; DFT calculations; guanidine-thiourea; Michael addition; organocatalysis; transition states; MOLECULAR-ORBITAL METHODS; GENERALIZED GRADIENT APPROXIMATION; DYNAMIC KINETIC RESOLUTION; DIRECT CONJUGATE ADDITION; GAUSSIAN-TYPE BASIS; BIFUNCTIONAL ORGANOCATALYSTS; ALPHA; BETA-UNSATURATED IMIDES; ELECTRON CORRELATION; CARBONYL-COMPOUNDS; DUAL ACTIVATION;
D O I：
10.3762/bjoc.8.168
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-beta-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.
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页码：1485 / 1498
页数：14
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