Catalytic asymmetric epoxidation of aliphatic enones using tartrate-derived magnesium alkoxides

被引:36
作者
Jacques, O
Richards, SJ
Jackson, RFW
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
D O I
10.1039/b109421a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple aliphatic enones can be converted into the corresponding epoxides in 71-93% ee using tert-butylhydroperoxide in the presence of a catalyst derived from dibutylmagnesium and di-tert-butyl tartrate.
引用
收藏
页码:2712 / 2713
页数:2
相关论文
共 11 条
[1]   Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes [J].
Bougauchi, M ;
Watanabe, S ;
Arai, T ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2329-2330
[2]   Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt [J].
Corey, EJ ;
Zhang, FY .
ORGANIC LETTERS, 1999, 1 (08) :1287-1290
[3]   Asymmetric epoxidation of chalcones with chirally modified lithium and magnesium tert-butyl peroxides [J].
Elston, CL ;
Jackson, RFW ;
MacDonald, SJF ;
Murray, PJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (04) :410-412
[4]   Asymmetric epoxidation of enones with oxygen in the presence of diethylzinc and (R,R)-N-methylpseudoephedrine [J].
Enders, D ;
Zhu, JQ ;
Raabe, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1725-1728
[5]  
Enders D, 1997, LIEBIGS ANN-RECL, P1101
[6]   MECHANISM OF ASYMMETRIC EPOXIDATION .2. CATALYST STRUCTURE [J].
FINN, MG ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :113-126
[7]   Efficient asymmetric epoxidation of α,β-unsaturated ketones using a soluble triblock polyethylene glycol-polyamino acid catalyst [J].
Flood, RW ;
Geller, TP ;
Petty, SA ;
Roberts, SM ;
Skidmore, J ;
Volk, M .
ORGANIC LETTERS, 2001, 3 (05) :683-686
[8]   Phase-transfer catalysed asymmetric epoxidation of enones using N-anthracenylmethyl-substituted cinchona alkaloids [J].
Lygo, B ;
Wainwright, PG .
TETRAHEDRON, 1999, 55 (20) :6289-6300
[9]   Catalytic asymmetric epoxidation of enones using La-BINOL-triphenylarsine oxide complex: Structural determination of the asymmetric catalyst [J].
Nemoto, T ;
Ohshima, T ;
Yamaguchi, K ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2725-2732
[10]   Asymmetric epoxidation of electron-deficient olefins [J].
Porter, MJ ;
Skidmore, J .
CHEMICAL COMMUNICATIONS, 2000, (14) :1215-1225