Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2H-Chromenes

被引：38

作者：

Luan, Yi

Sun, Huan

Schaus, Scott E. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 24期

关键词：

H BOND FUNCTIONALIZATION; ORTHO-QUINONE METHIDES; ALDER-TYPE ADDUCTS; ORGANIC-SYNTHESIS; ACID; DIMERIZATION; CYCLIZATION; EFFICIENT; CHROMENE; PHENOL;

D O I：

10.1021/ol202772k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.

引用

页码：6480 / 6483

页数：4

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