Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids

被引：30
作者：
Bortolini, O
Fantin, G
Fogagnolo, M
Forlani, R
Maietti, S
Pedrini, P
机构：
[1] Univ Ferrara, Dipartimento Chim, I-44100 Ferrara, Italy
[2] Dipartimento Risorse Nat & Culturali, I-44100 Ferrara, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 16期
关键词：
D O I：
10.1021/jo020146b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric epoxidation of substituted cinnamic acids has been obtained in the presence of different keto bile acid derivatives as optically active carbonyl inducers and Oxone as oxygen source. Predominant or almost exclusive formation of both enantiomeric epoxides is obtained (ee up to 95%) depending on the specific substitution at carbons C(7) and C(12) of the bile acid.
引用
收藏
页码：5802 / 5806
页数：5
相关论文
共 50 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]   Synthetic applications of nonmetal catalysts for homogeneous oxidations [J].
Adam, W ;
Saha-Möller, CR ;
Ganeshpure, PA .
CHEMICAL REVIEWS, 2001, 101 (11) :3499-3548
[4]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[5]   CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134
[6]  
AMSTRONG A, 1998, CHEM COMMUN, P621
[7]   ELECTRONIC-STRUCTURE AND REACTIVITY OF DIOXIRANE AND CARBONYL OXIDE [J].
BACH, RD ;
ANDRES, JL ;
OWENSBY, AL ;
SCHLEGEL, HB ;
MCDOUALL, JJW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7207-7217
[8]   INTRAMOLECULAR CATALYSIS .5. LONG-RANGE EFFECTS IN STEROIDS - ACETYLATION RATES OF SOME DELTA5-3BETA-HYDROXY STEROIDS [J].
BLICKENSTAFF, RT ;
SOPHASAN, K .
TETRAHEDRON, 1972, 28 (07) :1945-+
[9]   INTRAMOLECULAR CATALYSIS IN ACETYLATION OF METHYL CHOLATE [J].
BLICKENSTAFF, RT ;
ORWIG, B .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (05) :1377-+
[10]   A new non-enzymatic route to chenodeoxycholic acid [J].
Bortolini, O ;
Cova, U ;
Fantin, G ;
Medici, A .
CHEMISTRY LETTERS, 1996, (05) :335-336
12345