Organocatalytic asymmetric epoxidation of olefins by chiral ketones

被引：410
作者：
Shi, Y [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
ACCOUNTS OF CHEMICAL RESEARCH | 2004年 / 37卷 / 08期
关键词：
D O I：
10.1021/ar030063x
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral ketones have been shown to be effective organocatalysts for asymmetric epoxidation of olefins with broad substrate scope. High enantioselectivity has been obtained for a wide variety of trans and trisubstituted olefins, as well as a number of cis olefins, with encouragingly high ee's for some terminal olefins. The stereochemical outcome of the reaction can be rationalized by a spiro transition state model.
引用
收藏
页码：488 / 496
页数：9
相关论文
共 108 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]  
Adam W, 1996, B SOC CHIM BELG, V105, P581
[4]   Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane [J].
Adam, W ;
Fell, RT ;
Saha-Möller, CR ;
Zhao, CG .
TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :397-401
[5]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[6]  
Adam W., 2004, ORG REACTIONS, V61, P219, DOI DOI 10.1039/C3SC52649F
[7]  
Altmann KH, 2002, HELV CHIM ACTA, V85, P4086, DOI 10.1002/1522-2675(200211)85:11<4086::AID-HLCA4086>3.0.CO
[8]  
2-7
[9]  
[Anonymous], CATALYTIC ASYMMETRIC
[10]   EPOXIDATION OF ALKENES WITH TRICHLOROACETONITRILE HYDROGEN-PEROXIDE IN A NEUTRAL BIPHASIC SOLVENT SYSTEM [J].
ARIAS, LA ;
ADKINS, S ;
NAGEL, CJ ;
BACH, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :888-890
12345678910