ENANTIOSELECTIVE OPENING OF SPIRO EPOXIDES DERIVED FROM CIS BICYCLO[3.3.0]OCTAN-3,7-DIONE USING CHIRAL LITHIUM AMIDE BASES

被引：25

作者：

LEONARD, J ^{[1
]}

HEWITT, JD ^{[1
]}

OUALI, D ^{[1
]}

SIMPSON, SJ ^{[1
]}

NEWTON, RF ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)97152-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The monoketal derived from cis-bicyclo[3.3.0]octane-3,7-dione was converted to epoxides 3. The meso exo epoxide was cleaved via enantioselective deprotonation using chiral lithium amide bases to provide the synthetically useful alcohol 7 with up to 76%ee. The enantiomeric excess of the alcohol was determined by 1H NMR chiral shift techniques. © 1990.

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页码：6703 / 6706

页数：4

相关论文

共 11 条

[1] AN ASYMMETRIC TRANSFORMATION OF CYCLOHEXENE OXIDE TO (S)-2-CYCLOHEXEN-1-OL BY CHIRAL LITHIUM AMIDES [J].

ASAMI, M .

CHEMISTRY LETTERS, 1984, (05) :829-832

[2]

ASAMI M, 1990, JB CHEM SOC JPN, V63, P721

[3]

CAIN CM, 1989, TETRAHEDRON, V46, P523

[4] PREPARATION OF PROLINE DERIVED LITHIUM AMIDE BASES AND THEIR USE IN ENANTIOSELECTIVE DEPROTONATION OF MESO EPOXIDES [J].

HENDRIE, SK ;

LEONARD, J .

TETRAHEDRON, 1987, 43 (14) :3289-3294

[5] ENANTIOSELECTIVE DEPROTONATION OF THE MONOACETALS OF BICYCLO[3.3.0]OCTAN-3,7-DIONE - AN APPROACH TO THE ASYMMETRIC-SYNTHESIS OF CHIRAL SYNTHONS FOR CARBACYCLINS [J].

IZAWA, H ;

SHIRAI, R ;

KAWASAKI, H ;

KIM, H ;

KOGA, K .

TETRAHEDRON LETTERS, 1989, 30 (51) :7221-7224

[6] SYNTHESES OF OPTICALLY-ACTIVE BICYCLO[3.3.0]OCT-2-ENE DERIVATIVES BASED ON ASYMMETRIC ELIMINATION [J].

KASHIHARA, H ;

SUEMUNE, H ;

KAWAHARA, T ;

SAKAI, K .

TETRAHEDRON LETTERS, 1987, 28 (51) :6489-6492

[7] A SHORT ENANTIOSELECTIVE ROUTE TO CORYNANTHE ALKALOID PRECURSORS [J].

LEONARD, J ;

OUALI, D ;

RAHMAN, SK .

TETRAHEDRON LETTERS, 1990, 31 (05) :739-742

[8]

LEONARD J, IN PRESS TETRAHEDRON

[9] STEREOCHEMISTRY OF DECOMPOSITION OF N-NITROSO- AND N-AMINO-ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE [J].

OVERBERGER, C ;

HISKEY, RG ;

MARULLO, NP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (06) :1374-&

[10]

RAHMAN SK, 1988, THESIS U SALFORD