Stereoselective synthesis of tri- and tetrasubstituted alkenes by iron-catalyzed carbometalation ring-opening reactions of cyclopropenes

被引：66

作者：

Wang, Yi ^{[1
]}

Fordyce, Euan A. F.

Chen, Fung Yan ^{[1
]}

Lam, Hon Wai ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 38期

关键词：

alkenes; iron; nucleophilic addition; small ring systems; strained molecules;

D O I：

10.1002/anie.200802391

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Open sesame: An iron-catalyzed cyclopropene carbometalation ring-opening sequence using trialkylaluminum reagents is described. The reactions proceed with high levels of regio- and stereo-control to provide a range of multisubstituted alkenes, including trisubstituted vinylsilanes, trisubstituted vinylstannanes, and all-carbon tetrasubstituted alkenes. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7350 / 7353

页数：4

共 53 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2]

[Anonymous], 2007, ANGEW CHEM

[3] Allylgallation of cyclopropenes. Crystal structure of a novel cyclopropylgallium compound prepared by allylgallation of hydroxy-bearing cyclopropene [J].

Araki, S ;

Tanaka, T ;

Hirashita, T ;

Setsune, J .

TETRAHEDRON LETTERS, 2003, 44 (43) :8001-8003

[4] Stereoselective synthesis of halocyclopropanes via halogenation of cyclopropylindium reagents [J].

Araki, S ;

Kenji, O ;

Shiraki, F ;

Hirashita, T .

TETRAHEDRON LETTERS, 2002, 43 (45) :8033-8035

[5]

Araki S, 2001, CHEM-EUR J, V7, P2784, DOI 10.1002/1521-3765(20010702)7:13<2784::AID-CHEM2784>3.0.CO

[6]

2-A

[7] Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups [J].

Araki, S ;

Nakano, H ;

Subburaj, K ;

Hirashita, T ;

Shibutani, K ;

Yamamura, H ;

Kawai, M ;

Butsugan, Y .

TETRAHEDRON LETTERS, 1998, 39 (35) :6327-6330

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

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

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

[9] Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms [J].

Fallis, AG ;

Forgione, P .

TETRAHEDRON, 2001, 57 (28) :5899-5913

[10] Stereocontrolled synthesis of tetrasubstituted olefins [J].

Flynn, Alison B. ;

Ogilvie, William W. .

CHEMICAL REVIEWS, 2007, 107 (11) :4698-4745

← 1 2 3 4 5 6 →