π-facial diastereoselection in Diels-Alder reactions of (R)-4-[(p-tolylsulfinyl)methyl]quinols

被引：30

作者：

Carreño, MC ^{[1
]}

González, MP

Houk, KN

机构：

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

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 26期

关键词：

D O I：

10.1021/jo9712308

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total pi-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition-state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.

引用

页码：9128 / 9137

页数：10

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