LACTATE AS CHIRAL AUXILIARY IN ASYMMETRIC PHOTODECONJUGATION OF UNSATURATED ESTERS

被引：3

作者：

CHARLTON, JL ^{[1
]}

PHAM, VC ^{[1
]}

PETE, JP ^{[1
]}

机构：

[1] UFR SCI UNIV REIMS,REARRANGEMENTS THERM & PHOTOCHIM LAB,F-51062 REIMS,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)60009-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric photodeconjugation of the alpha,beta-unsaturated esters 1, 2 and 3, to the corresponding beta,gamma-unsaturated esters having a new chiral center at the alpha position, has been studied in a variety of solvents. In most solvents, the (S)-lactyl chiral auxiliary induced the S configuration at the new chiral center. However, irradiation of 1 in methanol or 2-propanol/water mixtures gave an unusual reversal of diastereoselectivity of produce the R configuration at the new chiral center.

引用

页码：6073 / 6076

页数：4

共 17 条

[1] REVERSAL OF DIASTEREOSELECTIVITY IN PROTONATION OF CHIRAL PHOTODIENOLS
AWANDI, D
HENIN, F
MUZART, J
PETE, JP
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (11) : 1101 - 1104
[2] CHARLTON JL, 1989, TETRAHEDRON LETT, V30, P3279
[3] DIELS-ALDER ADDITION OF THE FUMARATE AND ACRYLATE OF S-METHYL LACTATE TO ALPHA-HYDROXY ORTHOQUINODIMETHANES
CHARLTON, JL
PLOURDE, GL
KOH, K
SECCO, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (04): : 574 - 579
[4] HIGH STEREOSELECTIVITY IN LEWIS-ACID-CATALYZED AND UNCATALYZED DIELS-ALDER REACTIONS OF THE FUMARATE OF (S)-ETHYL LACTATE
HARTMANN, H
HADY, AFA
SARTOR, K
WEETMAN, J
HELMCHEN, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1143 - 1145
[5] Helmchen G, 1986, MODERN SYNTHETIC MET, V4, P261
[6] ENANTIOSELECTIVE PHOTODECONJUGATION OF CONJUGATED LACTONES INDUCED BY SMALL AMOUNTS OF A CHIRAL INDUCTOR
HENIN, F
MORTEZAEI, R
MUZART, J
PETE, JP
[J]. TETRAHEDRON LETTERS, 1985, 26 (40) : 4945 - 4948
[7] ENANTIOSELECTIVE PHOTODECONJUGATION OF CONJUGATED LACTONES AND ESTERS IN THE PRESENCE OF EPHEDRINE
HENIN, F
MORTEZAEI, R
MUZART, J
PETE, JP
PIVA, O
[J]. TETRAHEDRON, 1989, 45 (19) : 6171 - 6196
[8] ENANTIOSELECTIVE PHOTODECONJUGATION OF ALPHA-UNSATURATED, BETA-UNSATURATED ESTERS IN THE PRESENCE OF CATALYTIC AMOUNTS OF A CHIRAL-INDUCING ENTITY
MORTEZAEI, R
HENIN, F
MUZART, J
PETE, JP
[J]. TETRAHEDRON LETTERS, 1985, 26 (49) : 6079 - 6080
[9] EVALUATION OF THE STERIC INTERACTIONS RESPONSIBLE FOR THE ENANTIOSELECTIVE PHOTODECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS
MORTEZAEI, R
PIVA, O
HENIN, F
MUZART, J
PETE, JP
[J]. TETRAHEDRON LETTERS, 1986, 27 (26) : 2997 - 3000
[10] DIASTEREOSELECTIVE PHOTODECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS
MORTEZAEI, R
AWANDI, D
HENIN, F
MUZART, J
PETE, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4824 - 4826

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