ASYMMETRIC DIELS-ALDER REACTIONS WITH 5-MENTHYLOXY-2(5H)-FURANONE

被引：65

作者：

DEJONG, JC ^{[1
]}

VANBOLHUIS, F ^{[1
]}

FERINGA, BL ^{[1
]}

机构：

[1] UNIV GRONINGEN,DEPT ORGAN CHEM,NIJENBORG 16,9747 AG GRONINGEN,NETHERLANDS

来源：

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

关键词：

D O I：

10.1016/S0957-4166(00)80024-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed. Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol. Excellent diastereoselectivities (d.e. greater-than-or-equal-to 99%) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes. The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.

引用

页码：1247 / 1262

页数：16

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