Influence of diene substitution on Diels-Alder reactions between vinyl dihydronaphthalenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone

被引：9

作者：

Carreño, MC ^{[1
]}

García-Cerrada, S ^{[1
]}

Sanz-Cuesta, MJ ^{[1
]}

Urbano, A ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ C I, E-28049 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo0342774

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric Diels-Alder reaction between 2-(E-2-acetoxyvinyl)-8-tert-butyl-3,4-dihydronaphthalene (8) and enantiopure (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1) takes place exclusively on the unsubstituted C-5-C-6 double bond of (SS)-1 with a very high control of the chemo-, regio-, and diastereoselectivity of the process affording tetracyclic sulfinyl derivative 13a possessing five stereogenic centers. The analogue diene 9, lacking the tert-butyl group, gave a less chemoselective reaction (C-2-C-3/C-5-C-6: 60/40) in favor of reaction through the sulfoxide-substituted double bond C-2-C-3 of 1. Steric effects of the remote tert-butyl group and electronic factors due to the OAc substituent are controlling the process.

引用

页码：4315 / 4321

页数：7

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