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

收藏

页码：6480 / 6483

页数：4

相关论文

共 30 条

[1] MECHANISM AND STEREOCHEMISTRY OF THE ENZYME-CATALYZED FORMATION OF A 2,2-DIMETHYLCHROMENE RING FROM A PRENYLATED PHENOL - CONVERSION OF ROT-2'-ENONIC ACID INTO DEGUELIN BY DEGUELIN CYCLASE [J].

BHANDARI, P ;

CROMBIE, L ;

HARPER, MF ;

ROSSITER, JT ;

SANDERS, M ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13) :1685-1697

[2] Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide [J].

Bishop, Lee M. ;

Winkler, Michael ;

Houk, Kendall N. ;

Bergman, Robert G. ;

Trauner, Dirk .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) :5405-5408

[3] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[4] TOTAL SYNTHESIS OF CARPANONE [J].

CHAPMAN, OL ;

ENGEL, MR ;

SPRINGER, JP ;

CLARDY, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (24) :6696-&

[5] NMR kinetic investigations of the photochemical and thermal reactions of a photochromic chromene [J].

Delbaere, S ;

Micheau, JC ;

Vermeersch, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8968-8973

[6] Acid catalyzed stereoselective rearrangement and dimerization of flavenes: synthesis of dependensin [J].

Deodhar, Mandar ;

Black, David StC ;

Kumar, Naresh .

TETRAHEDRON, 2007, 63 (24) :5227-5235

[7] An efficient synthesis of novel tetrahydrochromeno[2,3-b]chromenes [J].

Devakaram, Ruth ;

Black, David Stc ;

Kumar, Naresh .

TETRAHEDRON LETTERS, 2010, 51 (28) :3636-3638

[8]

FUKAI T, 1985, CHEM PHARM BULL, V33, P3195

[9]

FUKAI T, 1984, HETEROCYCLES, V22, P1007

[10] Dual mechanisms of an organocatalytic homodimerization reaction [J].

Guidi, Vanina ;

Sandoval, Sergio ;

McGregor, Michael A. ;

Rosen, William .

TETRAHEDRON LETTERS, 2010, 51 (38) :5086-5090