Catalysis of 6π Electrocyclizations

被引：59

作者：

Bishop, Lee M. ^{[1
]}

Barbarow, Jennifer E. ^{[1
]}

Bergman, Robert G. ^{[1
]}

Trauner, Dirk ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 42期

基金：

美国国家科学基金会;

关键词：

cyclization; density functional calculations; homogeneous catalysis; pericyclic reaction; transition states;

D O I：

10.1002/anie.200803336

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Filling the gap: Lewis acid catalysis ofa 6π electrocyclization has been achieved for the first time (see scheme). DFT calculations were performed on the coordination ofa Lewis acid to a Lewis basic group in the 2-position ofa triene, and experimentally, the rates ofthe electrocyclization increase in the presence of Me2AlCl. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8100 / 8103

页数：4

共 32 条

[1] Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].

Aggarwal, VK ;

Beffield, AJ .

ORGANIC LETTERS, 2003, 5 (26) :5075-5078

[2] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].

Allred, GD ;

Liebeskind, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749

[3] SIMPLE-MODEL FOR PREDICTING EFFECT OF SUBSTITUENTS ON RATES OF THERMAL PERICYCLIC REACTIONS [J].

CARPENTER, BK .

TETRAHEDRON, 1978, 34 (13) :1877-1884

[4]

Corey E.J., 2002, ANGEW CHEM, V114, P1724, DOI DOI 10.1021/JACS.7B06567

[5]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[6]

2-B

[7] TRANSITION STRUCTURES OF THERMALLY ALLOWED DISROTATORY ELECTROCYCLIZATIONS - THE PREDICTION OF STEREOSELECTIVE SUBSTITUENT EFFECTS IN 6-ELECTRON PERICYCLIC-REACTIONS [J].

EVANSECK, JD ;

THOMAS, BE ;

SPELLMEYER, DC ;

HOUK, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7134-7141

[8]

Frisch M. J., 2004, GAUSSIAN 03 REVISION

[9] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

[10] Total synthesis of Iejimalide B [J].

Fuerstner, Alois ;

Nevado, Cristina ;

Tremblay, Martin ;

Chevrier, Carine ;

Teply, Filip ;

Aissa, Christophe ;

Waser, Mario .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5837-5842

← 1 2 3 4 →