THE DIASTEREOFACIAL SELECTIVITY IN THE INTRAMOLECULAR 1,4-CONJUGATE ADDITIONS GENERATING SUBSTITUTED TETRAHYDROTHIOPYRANS FOLLOWS THE CIEPLAK MODEL

被引:10
作者
GUNG, BW
FRANCIS, MB
机构
[1] Department of Chemistry, Miami University Oxford
关键词
D O I
10.1016/0040-4039(95)00344-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Alkyl-3-Alkoxytetrahydrothiopyrans were prepared by intramolecular Michael additions. The predominant cis product stereochemistry is consistent with the Cieplak model. A low-energy sigma(double dagger)* orbital originating from the sulfur nucleophile was proposed. The solvent effect was also discussed.
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页码:2579 / 2582
页数:4
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