Catalytic asymmetric epoxidation of α,β-unsaturated esters using an yttrium-biphenyidiol complex

被引:65
作者
Kakei, H [1 ]
Tsuji, R [1 ]
Ohshima, T [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja052466t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2-10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee. Copyright © 2005 American Chemical Society.
引用
收藏
页码:8962 / 8963
页数:2
相关论文
共 36 条
[11]  
Harada T, 1997, SYNLETT, P1426
[12]   Asymmetric desymmetrization of 2,2′,6,6′-tetrahydroxybiphenyl through annulation with enantiomerically pure bis(mesylate) [J].
Harada, T ;
Mai, T ;
Tuyet, T ;
Oku, A .
ORGANIC LETTERS, 2000, 2 (09) :1319-1322
[13]  
HARADA T, 1995, SYNLETT, P283
[14]   ASYMMETRIC-SYNTHESIS OF 6,6'-DIALKOXY-2,2'-BIPHENYLDIOLS BY USING MENTHONE AS A CHIRAL TEMPLATE [J].
HARADA, T ;
UEDA, S ;
YOSHIDA, T ;
INOUE, A ;
TAKEUCHI, M ;
OGAWA, N ;
OKU, A ;
SHIRO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7575-7576
[15]   General method for asymmetric synthesis of substituted 2,2'-biaryldiols via asymmetric desymmetrization of 2,2',6,6'-tetrahydroxybiphenyl with l-menthone [J].
Harada, T ;
Ueda, S ;
Tuyet, TMT ;
Inoue, A ;
Fujita, K ;
Takeuchi, M ;
Ogawa, N ;
Oku, A ;
Shiro, M .
TETRAHEDRON, 1997, 53 (49) :16663-16678
[16]   HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYSTS DERIVED FROM 1,2-DIAMINOCYCLOHEXANE [J].
JACOBSEN, EN ;
ZHANG, W ;
MUCI, AR ;
ECKER, JR ;
DENG, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7063-7064
[17]   ENANTIOSELECTIVE CATALYTIC EPOXIDATION OF CINNAMATE ESTERS [J].
JACOBSEN, EN ;
DENG, L ;
FURUKAWA, Y ;
MARTINEZ, LE .
TETRAHEDRON, 1994, 50 (15) :4323-4334
[18]   Direct catalytic asymmetric aldol reaction of hydroxyketones:: Asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex [J].
Kumagai, N ;
Matsunaga, S ;
Kinoshita, T ;
Harada, S ;
Okada, S ;
Sakamoto, S ;
Yamaguchi, K ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2169-2178
[19]   Catalytic asymmetric Michael reaction of β-keto esters:: Effects of the linker heteroatom in linked-BINOL [J].
Majima, K ;
Takita, R ;
Okada, A ;
Ohshima, T ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :15837-15845
[20]   Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes [J].
Matsunaga, S ;
Das, J ;
Roels, J ;
Vogl, EM ;
Yamamoto, N ;
Iida, T ;
Yamaguchi, K ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2252-2260