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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
KeywordAsymmetric Reduction Borane Electronic Effect Enantioselectivity Ketone
Source PublicationJOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
2008-04-02
DOI10.1016/j.molcata.2008.01.018
Volume284Issue:1-2Pages:40-45
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordHIGH ENANTIOSELECTIVITY ; PI-STACKING ; PROCHIRAL KETONES ; MECHANISM ; LIGANDS ; DIHYDROXYLATION ; HYDROGENATION ; AZIRIDINATION ; ACETOPHENONE ; SUBSTITUENTS
AbstractRationally 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.
Language英语
WOS IDWOS:000255189100006
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141150
Collection中国科学院大连化学物理研究所
Affiliation1.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
Recommended Citation
GB/T 7714
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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