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Unexpected influence and its origin in rationally tuning the electronic effect of catalysts in the asymmetric borane reduction of ketones
Du, Juanjuan1; Li, Zhiyi1; Du, Da-Ming1; Xu, Jiaxi1,2
关键词Asymmetric Reduction Borane Electronic Effect Enantioselectivity Ketone
刊名JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
2008-04-02
DOI10.1016/j.molcata.2008.01.018
284期:1-2页:40-45
收录类别SCI
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]HIGH ENANTIOSELECTIVITY ; PI-STACKING ; PROCHIRAL KETONES ; MECHANISM ; LIGANDS ; DIHYDROXYLATION ; HYDROGENATION ; AZIRIDINATION ; ACETOPHENONE ; SUBSTITUENTS
英文摘要Rationally tuning the electronic effect of catalysts is one of the most important strategies to improve stereoselectivity in asymmetric catalysis. (S)-2-aryl-3,1,2-oxazaborobicyclo[3.3.0] octanes, which can be considered as electronically tuned (S)-2-phenyl-3,1,2-oxazaborobicyclo[3.3.0] octane, were prepared and evaluated in the asymmetric borane reduction of ketones. An unexpected influence of the electronic effect of catalysts on the enantioselectivity was observed and attributed to the catalyst dimerization that was further confirmed experimentally. The unsuccessful tuning is accounted for by assuming that hydride transfer in the catalytic cycle is the rate-determining step in the reduction. catalyzed by B-aryl catalysts. (C) 2008 Published by Elsevier B.V.
语种英语
WOS记录号WOS:000255189100006
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/141150
专题中国科学院大连化学物理研究所
作者单位1.Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China
2.Beijing Univ Chem Technol, Coll Sci, Beijing 100029, Peoples R China
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Du, Juanjuan,Li, Zhiyi,Du, Da-Ming,et al. Unexpected influence and its origin in rationally tuning the electronic effect of catalysts in the asymmetric borane reduction of ketones[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL,2008,284(1-2):40-45.
APA Du, Juanjuan,Li, Zhiyi,Du, Da-Ming,&Xu, Jiaxi.(2008).Unexpected influence and its origin in rationally tuning the electronic effect of catalysts in the asymmetric borane reduction of ketones.JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL,284(1-2),40-45.
MLA Du, Juanjuan,et al."Unexpected influence and its origin in rationally tuning the electronic effect of catalysts in the asymmetric borane reduction of ketones".JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL 284.1-2(2008):40-45.
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