SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE

被引：26

作者：

ALONSO, I ^{[1
]}

CID, MB ^{[1
]}

CARRETERO, JC ^{[1
]}

RUANO, JLG ^{[1
]}

HOYOS, MA ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID CANTO BLANCO,DEPT QUIM C-I,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)80020-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure 2-p-tolylsulfinylmaleates 1, 2 and 3 have been readily prepared by Knoevenagel reaction between (S)-menthyl p-toluenesulfinate and glyoxylic acid. Their asymmetric Diels-Alder reactions with cyclopentadiene have been studied under a wide range of uncatalyzed and catalyzed conditions and the stereochemical results have been explained by assuming a steric control approach, in term of S-cis or S-trans favoured conformations. Uncatalyzed Diels-Alder reactions of 1 and some Lewis acid catalyzed Diels-Alder reactions of 2 show high facial and endo selectivities. The facial selectivity of dienophile 2 highly depends on the Lewis acid, whereas reactivity of 1 and 3 is very sensitive to the solvent. These sulfinylmaleates 1, 2 and 3 act as synthetic equivalents of chiral acetylenedicarboxylates in Diels-Alder reactions after basic elimination of the sulfinylic moiety in the resulting adducts.

引用

页码：1193 / 1207

页数：15

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