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Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives
其他题名Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives
Liu SS(刘莎莎); SANDOVAL CHRISTIAN A
2010
发表期刊J. Mol. Catal. A-Chem.
ISSN1381-1169
卷号325期号:1-2页码:65-72
摘要The calix[4]arene framework was readily modified to generate a number of chiral BINOL-based diphosphite ligands (3) capable of forming in situ Rh-complexes which catalyzed the asymmetric hydrogenation of model substrates methyl-(Z)-2-(acetamido)acrylate (1a) and methyl-(Z)-2-(acetamido)cinnamate (1b). The (S,S)-catalyst generated the (R)-product. Upper rim (R-1) and 1,3-O-alkylation (R-2) substitution on the calixarene strongly influenced catalyst activity and chiral induction. Optimum results were obtained when RI was -C(CH3)(3) and R-2 was -CH2CH2CH3 (3b). Under optimized conditions, 3b hydrogenated la and 1b in 98 and 96% ee, respectively. Overall, better catalyst performance was observed for "locked" cone-conformers of 3, with higher activity evident for the less sterically hindered 1a (TOF up to 1300h(-1) at P(H-2) = 5 atm). (C) 2010 Elsevier B.V. All rights reserved.
学科领域金属有机化学
部门归属天津大学; 中国科学院上海有机化学研究所
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收录类别SCI
语种英语
WOS记录号WOS:000278823300010
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被引频次:11[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27795
专题上海有机化学研究所
通讯作者SANDOVAL CHRISTIAN A
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Liu SS,SANDOVAL CHRISTIAN A. Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives[J]. J. Mol. Catal. A-Chem.,2010,325(1-2):65-72.
APA 刘莎莎,&SANDOVAL CHRISTIAN A.(2010).Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives.J. Mol. Catal. A-Chem.,325(1-2),65-72.
MLA 刘莎莎,et al."Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives".J. Mol. Catal. A-Chem. 325.1-2(2010):65-72.
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