CATALYTIC ASYMMETRIC RING-OPENING OF BRIDGED TRICYCLIC ANHYDRIDES

被引：67

作者：

AITKEN, RA

GOPAL, J

机构：

[1] Department of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, North Haugh

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80538-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cinchona alkaloid catalysed methanolysis of three different achiral tricyclic anhydrides provides convenient access to either enantiomer of the corresponding half-esters in 35-67% enantiomeric excess; the absolute configuration of the products has been determined and a convenient procedure developed for preparation of multigram quantities of either enantiomer of one half-ester in ∼90% e.e. © 1990.

引用

收藏

页码：517 / 520

页数：4

相关论文

共 12 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED COMPOUNDS WITH 6 CONTIGUOUS STEREOCENTERS [J].

AITKEN, RA ;

GOPAL, J ;

HIRST, JA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :632-634

[2]

Aitken Rob, UNPUB

[3] STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].

BLOCH, R ;

GUIBEJAMPEL, E ;

GIRARD, C .

TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090

[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[5]

GAIS HJ, 1986, LIEBIGS ANN CHEM, P687

[6] CATALYTIC ASYMMETRIC INDUCTION FROM PROCHIRAL CYCLIC ACID ANHYDRIDES USING CINCHONA ALKALOIDS [J].

HIRATAKE, J ;

YAMAMOTO, Y ;

ODA, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (23) :1717-1719

[7]

HIRATAKE J, 1987, J CHEM SOC P1, P1953

[8]

KAMETANI T, 1981, J CHEM SOC P1, P301

[9]

LIEB F, 1987, LIEBIGS ANN CHEM, P607

[10] ENZYMES IN ORGANIC-SYNTHESIS .34. PREPARATIONS OF ENANTIOMERICALLY PURE EXO-BRIDGED AND ENDO-BRIDGED BICYCLIC [2.2.1] AND [2.2.2] CHIRAL LACTONES VIA STEREOSPECIFIC HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF MESO DIOLS [J].

LOK, KP ;

JAKOVAC, IJ ;

JONES, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2521-2526