Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes

被引：29

作者：

Barluenga, J ^{[1
]}

Fernández-Rodríguez, MA ^{[1
]}

García-García, P ^{[1
]}

Aguilar, E ^{[1
]}

Merino, I ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, Oviedo 33006, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2006年 / 12卷 / 01期

关键词：

carbene ligands; carbenes; cyclopropanation; diastereoselectivity; microwave-accelerated reactions;

D O I：

10.1002/chem.200500918

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes (FCCs) represents a straightforward route to a new type of captodative (donor-acceptor) alkynylcyclopropanes, which have been prepared in moderate to high yields and in a diastereoselective manner. Some studies regarding the employment of additives to facilitate the recovery of the metal moiety after the reaction are also described. Finally, the first example of a cyclopropanation reaction through employing Fischer carbene complexes under microwave irradiation is presented; this method proved to be an advantageous alternative to the thermal reaction.

引用

页码：303 / 313

页数：11

共 112 条

[1]

ALVAREZTOLEDANO C, 1984, J CHEM SOC CHEM COMM, P574

[2]

[Anonymous], ANGEW CHEM

[3]

AUMANN R, 1993, SYNLETT, P667

[4]

Aumann R, 1999, EUR J ORG CHEM, V1999, P2545

[5] Nickel(0)-mediated [3+2+2] and [2+2+2+1] cyclization reactions of chromium Fischer carbene complexes and alkynes [J].

Barluenga, J ;

Barrio, P ;

López, LA ;

Tomás, M ;

García-Granda, S ;

Alvarez-Rúa, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (26) :3008-3011

[6] Cyclopropanation of alkenes mediated by novel chiral Fischer carbene complexes [J].

Barluenga, J ;

Muñiz, K ;

Ballesteros, A ;

Martínez, S ;

Tomás, M .

ARKIVOC, 2002, :110-119

[7] A novel [2+2+1]/[2+1] tandem cycloaddition reaction of Fischer alkynyl carbenes with strained bicyclic olefins [J].

Barluenga, J ;

Fernández-Rodríguez, MA ;

Andina, F ;

Aguilar, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10978-10979

[8] The [2+1] and [4+3] cyclization reactions of fulvenes with Fischer carbene complexes:: New access to annulated cyclopentanones [J].

Barluenga, J ;

Martínez, S ;

Suárez-Sobrino, AL ;

Tomás, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5948-5949

[9] Diastereo- and enantioselective cyclopropanation with chromium Fischer carbene complexes:: Alkenyl oxazolines as useful achiral and chiral substrates [J].

Barluenga, J ;

Suárez-Sobrino, AL ;

Tomás, M ;

García-Granda, S ;

Santiago-García, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10494-10501

[10]

Barluenga J, 2001, CHEM-EUR J, V7, P4723, DOI 10.1002/1521-3765(20011105)7:21<4723::AID-CHEM4723>3.0.CO

← 1 2 3 4 5 6 7 8 9 10 →