Bifunctionalized allenes, VII: Two methods for one-pot synthesis of sulfonyl-functionalized allenecarboxylates and phosphorylated allenes

被引：13

作者：

Christov, Valerij C. ^{[1
]}

Ivanova, Jordanka G. ^{[1
]}

机构：

[1] Univ Shumen, Dept Chem, BG-9700 Shumen, Bulgaria

来源：

SYNTHETIC COMMUNICATIONS | 2006年 / 36卷 / 15期

关键词：

2,3]-sigmatropic rearrangement; 1-sulfonyl-alka-1,2-dienephosphonates; 1-sulfonyl-alka-1,2-dienyl phosphine oxides; 2-sulfonyl-alka-2,3-dienoates; synthesis;

D O I：

10.1080/00397910600639042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new approaches to the synthesis of sulfonyl-functionalized allenecarboxylates and phosphorylated allenes are described. 2-Sulfonyl-alka-2,3-dienoates were readily prepared in an one-pot reaction by [2,3]-sigmatropic rearrangement of sulfinato-substituted 2-alkynoates, in situ generated from ethyl propynoate and subsequent treatment with lithium diisopropyl (LDA), ketone, trimethylchlorosilane (TMSCl), and the corresponding sulfinyl chlorides. Preparation of 1-sulfonyl-alka-1,2-dienephosphonates and -1,2-dienyl phosphine oxides consists of the reaction of the lithio compounds, in situ generated from phosphorylated allenes and LDA, with the corresponding sulfonyl chlorides.

引用

页码：2231 / 2244

页数：14

共 75 条

[51] Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans via PdCl2-catalyzed coupling-cyclization reaction of 2,3-allenols with allylic halides [J].