DICP OpenIR
Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones
Wang, Jin1; Liu, Han1; Du, Da-Ming1,2
Source PublicationTETRAHEDRON-ASYMMETRY
2009-05-25
DOI10.1016/j.tetasy.2009.02.057
Volume20Issue:5Pages:605-609
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
WOS Research AreaChemistry
WOS KeywordFRIEDEL-CRAFTS ALKYLATION ; ENANTIO-SELECTIVE ADDITION ; ENANTIOSELECTIVE REDUCTION ; BIS(OXAZOLINE) LIGANDS ; CHIRAL PHOSPHINAMIDES ; MICHAEL ADDITION ; AROMATIC KETONES ; FACILE SYNTHESIS ; AMIDE) LIGANDS ; SQUARIC ACID
AbstractA series of bis-hydroxyamides were synthesized from diphenylamine-2,2'-dicarboxylic acid and chiral aminoalcohols. Their catalytic activity in asymmetric borane reduction was investigated. After the fine optimization of solvents, temperature, amount of borane complex, and the length of catalyst generating period, good to excellent yields (55-99%) and enantioselectivities (79-97% ee) can be achieved in the reduction of aromatic and alkyl prochiral ketones. A transition state structure was proposed on the basis of absolute configuration and controlled experiment. (C) 2009 Elsevier Ltd. All rights reserved.
Language英语
WOS IDWOS:000266526100011
Citation statistics
Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141446
Collection中国科学院大连化学物理研究所
Affiliation1.Peking Univ, Coll Chem & Mol Engn, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
2.Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
Recommended Citation
GB/T 7714
Wang, Jin,Liu, Han,Du, Da-Ming. Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones[J]. TETRAHEDRON-ASYMMETRY,2009,20(5):605-609.
APA Wang, Jin,Liu, Han,&Du, Da-Ming.(2009).Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones.TETRAHEDRON-ASYMMETRY,20(5),605-609.
MLA Wang, Jin,et al."Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones".TETRAHEDRON-ASYMMETRY 20.5(2009):605-609.
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