REVERSAL OF DIASTEREOSELECTIVITY IN PROTONATION OF CHIRAL PHOTODIENOLS

被引：20

作者：

AWANDI, D

HENIN, F

MUZART, J

PETE, JP

机构：

[1] Laboratoire des Réarrangements Thermiques et Photochimiques, Unité Associée au CNRS, Université de Reims Champagne-Ardenne, 51062 Reims Cédex

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)82006-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The configuration of the new asymmetric center created in the photodeconjugation of an alpha-substituted alpha,beta-unsaturated ester derived from exo, exo-benzyloxybornanol depends on the structure of the achiral species used as the catalyst of the protonation of the intermediate dienol. Thus, the ratio of the deconjugated diastereoisomers varies from 91/9 to 37/63.

引用

页码：1101 / 1104

页数：4

共 18 条

[1] CONVERSION OF ALPHA,BETA-UNSATURATED ESTERS TO THEIR BETA,GAMMA-UNSATURATED ISOMERS BY PHOTOCHEMICAL DECONJUGATION [J].

DUHAIME, RM ;

LOMBARDO, DA ;

SKINNER, IA ;

WEEDON, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :873-879

[2] ENANTIOSELECTIVE DEPROTONATION OF 2 RACEMIC CYCLIC CARBONYL-COMPOUNDS BY A CHIRAL LITHIUM AMIDE [J].

ELEVELD, MB ;

HOGEVEEN, H .

TETRAHEDRON LETTERS, 1986, 27 (05) :631-634

[3] ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-ESTERS VIA ESTER ENOLATES [J].

GAMBONI, R ;

MOHR, P ;

WAESPESARCEVIC, N ;

TAMM, C .

TETRAHEDRON LETTERS, 1985, 26 (02) :203-206

[4]

HELMCHEN G, 1974, TETRAHEDRON LETT, P1527

[5] ENANTIOSELECTIVE PHOTODECONJUGATION OF CONJUGATED LACTONES AND ESTERS IN THE PRESENCE OF EPHEDRINE [J].

HENIN, F ;

MORTEZAEI, R ;

MUZART, J ;

PETE, JP ;

PIVA, O .

TETRAHEDRON, 1989, 45 (19) :6171-6196

[6]

HOREAU A, 1961, TETRAHEDRON LETT, P506

[7] STEREOCHEMISTRY OF ALIPHATIC CARBOCATIONS .9. SUBSTITUENT EFFECTS IN 1,2 HYDRIDE SHIFTS [J].

KIRMSE, W ;

FEYEN, P ;

GRUBER, W ;

KAPMEYER, W .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (06) :1839-1854

[8] ALPHA,BETA-UNSATURATED OXAZOLINES, A POWERFUL TOOL IN ASYMMETRIC DIELS-ALDER CYCLOADDITIONS [J].

KOUKLOVSKY, C ;

POUILHES, A ;

LANGLOIS, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6672-6679

[9]

LIU HH, 1990, TETRAHEDRON LETT, V31, P257

[10] EVALUATION OF THE STERIC INTERACTIONS RESPONSIBLE FOR THE ENANTIOSELECTIVE PHOTODECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS [J].

MORTEZAEI, R ;

PIVA, O ;

HENIN, F ;

MUZART, J ;

PETE, JP .

TETRAHEDRON LETTERS, 1986, 27 (26) :2997-3000

← 1 2 →