Functionalized 1-alkoxy-1,3-dienes: Their preparation and applications in synthetic organic

被引：43

作者：

Deagostino, Annamaria ^{[1
]}

Prandi, Cristina ^{[1
]}

Zavattaro, Chiara ^{[1
]}

Venturello, Paolo ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 11期

关键词：

arylation; conjugation; cross-coupling; dienes; elimination;

D O I：

10.1002/ejoc.200500944

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of various alpha,beta-unsaturated acetals with two equivalents of the Schlosser reagent LIC-KOR [equimolar mixture of BuLi (LIC), and tBuOK (KOR)] gives 1-metalated (1E)-1-alkoxy-1,3-dienes. These products can be transformed into trienic derivatives that are apt to participate in intramolecular Diels-Alder (IMDA) cycloaddition reactions, and can also be transformed into bifunctional (gamma-halo-alpha-carbonyl) reagents. Moreover, the metalated dienes can be readily functionalized with suitable electrophiles to afford products that have been found to be useful reagents for the Stille and Suzuki cross-coupling reactions or arylated according to the conditions of the Heck process. Other significant syntheses of dienic and polyenic structures are reported along with some of their applications in organic synthesis.

引用

页码：2463 / 2483

页数：21

共 119 条

[1] Stereocontrolled synthesis of retinoids functionalized at C-13 by Suzuki coupling reactions [J].