New Regiospecific Synthesis of Tri- and Tetra-Substituted Furans

被引：35

作者：

Sydnes, Leiv K. ^{[1
]}

Holmelid, Bjarte ^{[1
]}

Sengee, Myagmarsuren ^{[1
,2
]}

Hanstein, Miriam ^{[1
,3
]}

机构：

[1] Univ Bergen, Dept Chem, NO-5007 Bergen, Norway

[2] Natl Univ Mongolia, Dept Organ Chem, Ulaanbaatar 210646, Mongolia

[3] Tech Univ Dortmund, Fak Chem & Bioanorgan Chem, DE-44227 Dortmund, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 09期

关键词：

ACCELERATED CONJUGATE ADDITION; BETA-UNSATURATED KETONES; ONE-POT SYNTHESIS; LITHIUM DIMETHYLCUPRATE; ALPHA; BETA-UNSATURATED ESTERS; NUCLEOPHILIC-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; EFFICIENT SYNTHESIS; ACETYLENIC ACETALS;

D O I：

10.1021/jo9003986

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Acyloxy alpha,beta-unsaturated acetylenic ketones have been shown to react with organocuprate reagents and undergo cyclization followed by dehydration to give substituted furans as the final products. The transformation appeared to be versatile, and tri- and tetra-substituted furans were obtained, with regiochemical control in moderate to good yields. The best yields were generally obtained when the reactions were performed around -60 degrees C with substrates and cuprates containing sterically demanding substituents. The proposed mechanism for furan formation has been supported by experiments.

引用

页码：3430 / 3443

页数：14

共 99 条

[91] THE MECHANISM OF ORGANOCUPRATE 1,4-ADDITION REACTIONS WITH ALPHA-BETA-UNSATURATED KETONES - FORMATION OF CUPRATE-ENONE COMPLEXES WITH LITHIUM DIMETHYLCUPRATE [J].