ASYMMETRIC DIELS-ALDER REACTIONS - INVERSE ELECTRON DEMAND REACTIONS OF ESTERS OF 3-HYDROXYPYRAN-2-ONE WITH VINYL ETHERS - USE OF HIGH-PRESSURE TO AVOID DECARBOXYLATION OF ADDUCTS

被引：20

作者：

PRAPANSIRI, V ^{[1
]}

THORNTON, ER ^{[1
]}

机构：

[1] UNIV PENN, DEPT CHEM, PHILADELPHIA, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 27期

关键词：

DIELS ALDER; ASYMMETRIC; PYRAN-2-ONE; VINYL ETHER; HIGH-PRESSURE;

D O I：

10.1016/S0040-4039(00)79707-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric inverse electron-demand Diels-Alder reactions of esters of 3-hydroxypyran-2-one with vinyl ethers proceed under high pressure at ambient temperature, making isolation of the synthetically useful bicyclic adducts feasible. Investigation has revealed that the desired adduct can be synthesized with diastereofacial selectivity, up to 88:12, by reaction of the acetate of 3-hydroxypyran-2-one with chiral 8-(3,5-dimethylphenyl)menthyl vinyl ether.

引用

页码：3147 / 3150

页数：4

共 24 条

[1] CORRELATION OF SOLVENT EFFECTS ON STEREOSELECTIVITIES OF DIELS-ALDER REACTIONS BY MEANS OF LINEAR FREE ENERGY RELATIONSHIPS - A NEW EMPIRICAL MEASURE OF SOLVENT POLARITY [J].