A CHELATION-CONTROLLED ESTER ENOLATE CLAISEN REARRANGEMENT

被引：17

作者：

KRAFFT, ME

DASSE, OA

JARRETT, S

FIEVRE, A

机构：

[1] Department of Chemistry, The Florida State University, Tallahassee

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 16期

关键词：

D O I：

10.1021/jo00121a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.

引用

页码：5093 / 5101

页数：9

共 43 条

[1]

AZACLAISEN TT, 1990, TETRAHEDRON LETT, V31, P727

[2]

BARTLETT PA, 1980, TETRAHEDRON, V36, P2

[3]

BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589

[4] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS [J].