Enantioenriched (S)-6,6′-diphenylbinol-Ca:: a novel and efficient chirally modified metal complex for asymmetric epoxidation of α,β-unsaturated enones

被引:45
作者
Kumaraswamy, G [1 ]
Sastry, MNV
Jena, N
Kumar, KR
Vairamani, M
机构
[1] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Natl Ctr Mass Spectrometry, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/j.tetasy.2003.08.022
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel enantioenriched-Ca complex was generated using low cost commercially available CaCl, and the potassium salt of (S)-6,6'-diphenylBINOL and its application to alpha,beta-unsaturated enone epoxidation is described. Furthermore the absolute stereochemistry of (S)-6,6'-diphenylBINOL has been corrected and unequivocally established by single crystal X-ray analysis, 500 MHz NMR spectroscopy and mass spectra. The enantiomeric excess (ee) was determined by H-1 NMR spectroscopy of its corresponding MTPA ester and was found to be >98%. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3797 / 3803
页数:7
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