ENANTIOSELECTIVE EPOXIDATION OF UNFUNCTIONALIZED OLEFINS WITH MOLECULAR-OXYGEN AND ALDEHYDE CATALYZED BY OPTICALLY-ACTIVE MANGANESE(III) COMPLEXES

被引：145

作者：

YAMADA, T

IMAGAWA, K

NAGATA, T

MUKAIYAMA, T

机构：

来源：

CHEMISTRY LETTERS | 1992年 / 11期

关键词：

D O I：

10.1246/cl.1992.2231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective epoxidation of unfunctionalized olefins with combined use of molecular oxygen, an oxidant, and pivalaldehyde, a reductant, was demonstrated in the presence of a catalytic amount of optically active Mn(III)-salen complexes. Dihydronaphthalene derivatives were converted into the corresponding optically active epoxides in good yields with 60-77% enantiomeric excesses.

引用

收藏

页码：2231 / 2234

页数：4

相关论文

共 26 条

[1] OPTICALLY ACTIVE 1,2-NAPHTHALENE OXIDE [J].

BOYD, DR ;

JERINA, DM ;

DALY, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (09) :3170-&

[2] BACTERIAL METABOLISM OF 6,7-DIHYDRO-5H-BENZOCYCLOHEPTENE BY PSEUDOMONAS-PUTIDA - SYNTHESIS AND ABSOLUTE-CONFIGURATION OF BENZYLIC ALCOHOL AND CIS-DIOL METABOLITES OF 6,7-DIHYDRO-5H-BENZOCYCLOHEPTENE [J].

BOYD, DR ;

DORRITY, MRJ ;

MALONE, JF ;

MCMORDIE, RAS ;

SHARMA, ND ;

DALTON, H ;

WILLIAMS, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :489-494

[3] ENDOCYCLIC ALPHA,BETA-UNSATURATED KETONES .4. REACTION OF 4,4-DIMETHYL-1-KETO-1,4-DIHYDRONAPHTHALENE WITH CYCLOHEXYLMAGNESIUM BROMIDE [J].

CAMPBELL, RD ;

CROMWELL, NH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (19) :5169-5171

[4] A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE-B-(1) [J].

COREY, EJ ;

MARFAT, A ;

MUNROE, J ;

KIM, KS ;

HOPKINS, PB ;

BRION, F .

TETRAHEDRON LETTERS, 1981, 22 (12) :1077-1080

[5] STABLE ALPHA-CHLORO-BETA-OXOSULFENYL CHLORIDES - NOVEL CLASS OF COMPOUNDS FORMED FROM KETONES AND THIONYL CHLORIDE [J].

CROSSLAND, I .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (08) :787-789

[6]

FURUHASHI K, 1984, APPL MICROBIOL BIOT, V20, P6

[7] CATALYTIC ASYMMETRIC EPOXIDATIONS WITH CHIRAL IRON PORPHYRINS [J].

GROVES, JT ;

MYERS, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5791-5796

[8] OXOVANADIUM(IV) COMPLEX CATALYZED OXYGENATION OF ALPHA,BETA-UNSATURATED CARBOXAMIDE INTO 2,3-EPOXYCARBOXAMIDE WITH MOLECULAR-OXYGEN AND AN ALDEHYDE [J].

INOKI, S ;

TAKAI, T ;

YAMADA, T ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1991, (06) :941-944

[9] CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS [J].

IRIE, R ;

NODA, K ;

ITO, Y ;

MATSUMOTO, N ;

KATSUKI, T .

TETRAHEDRON LETTERS, 1990, 31 (50) :7345-7348

[10]

IRIE R, 1991, SYNLETT, P265