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

[11] MORTEZAEI R, 1987, PHOTODECONJUGAISON A
[12] ENANTIOSELECTIVE PHOTODECONJUGATION OF CONJUGATED ESTERS AND LACTONES
PETE, JP
HENIN, F
MORTEZAEI, R
MUZART, J
PIVA, O
[J]. PURE AND APPLIED CHEMISTRY, 1986, 58 (09) : 1257 - 1262
[13] PETE JP, 1992, IN PRESS TETRAHEDRON, P3
[14] ENANTIOSELECTIVE PHOTODECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS - EFFECT OF THE NATURE OF THE CHIRAL AGENT
PIVA, O
HENIN, F
MUZART, J
PETE, JP
[J]. TETRAHEDRON LETTERS, 1986, 27 (26) : 3001 - 3004
[15] HIGHLY ENANTIOSELECTIVE PHOTODECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS - ORIGIN OF THE CHIRAL DISCRIMINATION
PIVA, O
MORTEZAEI, R
HENIN, F
MUZART, J
PETE, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) : 9263 - 9272
[16] HIGHLY ENANTIOSELECTIVE PROTONATION OF PHOTODIENOLS AN UNUSUAL SUBSTITUENT EFFECT ON THE INDUCED CHIRALITY
PIVA, O
PETE, JP
[J]. TETRAHEDRON LETTERS, 1990, 31 (36) : 5157 - 5160
[17] PIVA O, 1987, TETRAHEDRON LETT, V28, P2845

← 1 2 →