Synthesis and characterization of (5R,6R)-6-Pheny1-5-(phenyl-sulfonylacetyl)bicyclo[2.2.1]hept-2-ene

被引：0

作者：

Pei, Wen ^{[1
]}

Sun, Li ^{[1
]}

Wang, Hai-Bin ^{[1
]}

Wang, Yong-Jiang ^{[1
]}

Shao, Yue-Shui ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat, Hangzhou 310014, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 26卷 / 05期

关键词：

asymmetric catalysis; Diels-Alder reaction; crystal structure; phenylsulfonyl unsaturated ketone; synthesis; mechanism;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for preparation of 4-phenyl-1-phenylsulfonyl-3-butene-2-one was developed. 1-Bromo-4-phenyl-3-butene-2-one was obtained by the bromination of 4-phenyl-3-butene-2-one with Ph3P+CH2CH2COOHBr3-, then reacted with sodium benzene sulfinate directly to give 4-phenyl-1-phenylsulfonyl-3-butene-2-one in good yield. (5R,6R)-6-Phenyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene with > 99% ee was obtained by the asymmetric Diels-Alder reaction of 4-phenyl-1-phenylsulfonyl-3-butene-2-one with cyclopentadiene catalyzed by chiral titanium reagent. The asymmetric reaction mechanism was discussed and the adduct was characterized by X-ray, IR, MS and NMR spectra.

引用

页码：727 / 729

页数：3