Influence of the sulfinyl group on the chemoselectivity and pi-facial selectivity of Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone

被引：58
作者：
Carreno, MC
Ruano, JLG
Toledo, MA
Urbano, A
Remor, CZ
Stefani, V
Fischer, J
机构：
[1] UNIV FED RIO GRANDE SUL,INST QUIM,PORTO ALEGRE,RS,BRAZIL
[2] UNIV STRASBOURG 1,UA 424,CRISTALLOCHIM LAB,F-67070 STRASBOURG,FRANCE
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期
关键词：
D O I：
10.1021/jo951438y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.
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页码：503 / 509
页数：7
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