ICCAS OpenIR
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
2008-04-02
Source PublicationJOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
ISSN1381-1169
Volume284Issue:1-2Pages:40-45
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.
KeywordAsymmetric Reduction Borane Electronic Effect Enantioselectivity Ketone
DOI10.1016/j.molcata.2008.01.018
Indexed BySCI
Language英语
WOS IDWOS:000255189100006
PublisherELSEVIER SCIENCE BV
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/65180
Collection中国科学院化学研究所
Corresponding AuthorXu, Jiaxi
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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