FeCl3-catalyzed tandem Prins and Friedel-Crafts cyclization: a highly diastereoselective route to polycyclic ring structures

被引：17

作者：

Ghosh, Arun K. ^{[1
]}

Keyes, Chad

Veitschegger, Anne M.

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 30期

基金：

美国国家卫生研究院;

关键词：

FeCl3; catalysis; Isochromene; Prins cyclization; Friedel-Crafts reaction; CBS reduction; STEREOSELECTIVE-SYNTHESIS; ACCESS; IRON;

D O I：

10.1016/j.tetlet.2014.05.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic FeCl3 in the presence of 4 A molecular sieves has been shown to effect highly diastereoselective tandem Prins and Friedel-Crafts cyclization of substituted (E/Z)-6-phenylhex-3-en-1-ol and a variety of aldehydes to provide a range of polycyclic compounds in good to excellent yields. The reaction of an enantioenriched alcohol with an aldehyde provided the cyclization product without loss of optical activity. Furthermore, a Lewis acid catalyzed ring opening resulted in functionalized tetralin derivatives with multiple chiral centers. Published by Elsevier Ltd.

引用

页码：4251 / 4254

页数：4

共 31 条

[1]

[Anonymous], 997772 CCDC

[2]

[Anonymous], 997771 CCDC

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