Ketone-catalyzed asymmetric epoxidation reactions

被引:213
作者
Yang, D [1 ]
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1021/ar030065h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This Account summarizes our efforts in developing organic ketone catalysts for enantioselective and diastereoselective epoxidation of olefins. We have developed an efficient and general protocol for epoxidation of olefins using dioxiranes generated in situ from activated ketones and Oxone (2KHSO(5).KHSO4.K2SO4) in a homogeneous aqueous solvent system. We have also developed chiral ketone catalysts for highly enantioselective epoxidation of unfunctionalized trans-olefins and trisubstituted olefins. Excellent diastereoselectivities have been achieved for epoxidation of substituted cyclohexenes with ketone catalysts.
引用
收藏
页码:497 / 505
页数:9
相关论文
共 74 条
[1]   Synthesis of optically active C2-symmetric ketones for the asymmetric epoxidation of prochiral olefins by dioxiranes generated in situ with Caroate™ as a peroxide source [J].
Adam, W ;
Zhao, CG .
TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :3995-3998
[2]   Asymmetric epoxidation of olefins by chiral dioxiranes generated in situ from ketones of D-(-)-quinic acid [J].
Adam, W ;
Saha-Möller, CR ;
Zhao, CG .
TETRAHEDRON-ASYMMETRY, 1999, 10 (14) :2749-2755
[3]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[4]  
ADAM W, 1993, TOP CURR CHEM, V164, P45
[5]  
AGGARWAL VK, 1999, COMPREHENSIVE ASYMME, V2, pCH18
[6]  
Altmann KH, 2002, HELV CHIM ACTA, V85, P4086, DOI 10.1002/1522-2675(200211)85:11<4086::AID-HLCA4086>3.0.CO
[7]  
2-7
[8]   Asymmetric epoxidation catalyzed by esters of α-hydroxy-8-oxabicyclo[3.2.1]octan-3-one [J].
Armstrong, A ;
Moss, WO ;
Reeves, JR .
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2779-2781
[9]   Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone [J].
Armstrong, A ;
Hayter, BR .
CHEMICAL COMMUNICATIONS, 1998, (05) :621-622
[10]   Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids [J].
Bortolini, O ;
Fantin, G ;
Fogagnolo, M ;
Forlani, R ;
Maietti, S ;
Pedrini, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5802-5806