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.
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页码：488 / 496
页数：9
相关论文
共 108 条
[51]  
Katsuki T., 1996, ORG REACT, V48, P1, DOI 10.1002/0471264180.or048.01
[52]  
Katsuki T., 2000, CATALYTIC ASYMMETRIC, P287
[53]   2-Substituted-2,4-endo-dimethyl-8-oxabicyclo[3.2.1]octan-3-ones as catalysts for the asymmetric epoxidation of some alkenes with Oxone® [J].
Klein, S ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2686-2691
[54]   Electron transfer initiated heterogenerative cascade cyclizations: Polyether synthesis under nonacidic conditions [J].
Kumar, VS ;
Aubele, DL ;
Floreancig, PE .
ORGANIC LETTERS, 2002, 4 (15) :2489-2492
[55]  
Lauret C, 2002, ALDRICHIM ACTA, V35, P47
[56]   Asymmetric ylide reactions: Epoxidation, cyclopropanation, aziridination, olefination, and rearrangement [J].
Li, AH ;
Dai, LX ;
Aggarwal, VK .
CHEMICAL REVIEWS, 1997, 97 (06) :2341-2372
[57]   Stereocontrolled synthesis of bicyclic lactone derivatives via tungsten-mediated [3+2] cycloaddition of epoxides with a tethered alkynyl group [J].
Madhushaw, RJ ;
Li, CL ;
Su, HL ;
Hu, CC ;
Lush, SF ;
Liu, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1872-1877
[58]   Chiral ketone-catalyzed asymmetric epoxidation of olefins with Oxone® [J].
Matsumoto, K ;
Tomioka, K .
TETRAHEDRON LETTERS, 2002, 43 (04) :631-633
[59]   Concise, regioselective synthesis of the ABC tristetrahydropyran of thyrsiferol and venustatriol [J].
McDonald, FE ;
Wei, XD .
ORGANIC LETTERS, 2002, 4 (04) :593-595
[60]   Endo-oxacyclizations of polyepoxides:: Biomimetic synthesis of fused polycyclic ethers [J].
McDonald, FE ;
Bravo, F ;
Wang, X ;
Wei, XD ;
Toganoh, M ;
Rodríguez, JR ;
Do, B ;
Neiwert, WA ;
Hardcastle, KI .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2515-2523
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