INTRAMOLECULAR DIELS-ALDER REACTIONS VIA SULFONE-SUBSTITUTED 3-SULFOLENES

被引：19

作者：

CHOU, SSP

LEE, CS

CHENG, MC

TAI, HP

机构：

[1] Department of Chemistry, Fu Jen Catholic University, Taipei

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regiospecific alkylation of the dianion of sulfone-substituted 3-sulfolenes 1-4 attached an unsaturated alkyl chain at the C2 position to form convenient precursors for IMDA reactions. The substituents on the diene moiety have a significant effect on the reactivity of the IMDA reactions (H) Me(3)Si > PhS). The stereochemistry of the cyclization reaction depends on the chain length connecting the diene and dienophile. The hydronaphthalene products 12a and 12b are obtained only in the trans form, and the hydroindene products 10 and 11 have predominantly the trans ring structure. All the products have the useful vinylic sulfone structure.

引用

页码：2010 / 2013

页数：4

共 61 条

[31] COMPLETE REGIOSPECIFICITY AND STEREOSPECIFICITY IN THE LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS OF (Z)-2-METHOXY-1-(PHENYLTHIO)-1,3-BUTADIENES - CONVERSION OF THE CS-CONFIGURATION OF AN ADDUCT TO THE CC-CONFIGURATION AT THE ALLYLIC POSITION BY A [2,3] SIGMATROPIC REARRANGEMENT [J].