Carbohydrate-derived dienes for intramolecular and asymmetric Diels-Alder reactions

被引：11

作者：

Areces, P ^{[1
]}

Jiménez, JL ^{[1
]}

Pozo, MDC ^{[1
]}

Román, E ^{[1
]}

Serrano, JA ^{[1
]}

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 07期

关键词：

D O I：

10.1039/b006078j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Acyloxydienes 2 and 10, derived from tri-O-acetyl-D-glucal are converted into appropriate substrates to perform intramolecular Diels-Alder reactions, thus yielding cis- or trans-fused bicyclic compounds. Attempts are made to rationalize the observed ratios between cycloadducts, as well as those previously reported in the literature for related experiments, by theoretical studies at the PM3 semiempirical level. In addition, the new chiral diene 9 derived from D-galactose or D-mannose, via an aldehydo-heptose, is obtained; the Diels-Alder reaction of 9 with N-phenylmaleimide is studied, and the observed asymmetric induction is explained by PM3 and B3LYP/6-31G* calculations.

引用

页码：754 / 762

页数：9

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