A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3+2] cyclization of alkenyl Fischer carbene complexes and internal alkynes

被引：49

作者：

Barluenga, Jose ^{[1
]}

Barrio, Pablo ^{[1
]}

Riesgo, Lorena ^{[1
]}

Lopez, Luis. A. ^{[1
]}

Tomas, Miguel ^{[1
]}

机构：

[1] Univ Oviedo, CSIC, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada, E-33071 Oviedo, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 46期

关键词：

D O I：

10.1021/ja075106+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A broad range of substituted 2-cyclopentenone derivatives 3-6 are synthesized by the nickel-(0)-mediated [3 + 2] cyclization reaction of chromium alkenyl(methoxy)carbene complexes 1 and internal alkynes 2. The reaction takes place with complete regioselectivity with both unactivated alkynes and activated alkynes (electron-withdrawing and electron-donating substituted alkynes). Representative cycloadducts containing boron and tin substituents are further demonstrated to be active partners in classical Pd-catalyzed C-C coupling processes to allow the production of 2-aryl- and 2-alkynyl-substituted cyclopentenones 9-13.

引用

页码：14422 / 14426

页数：5

共 50 条

[1] Low-energy pathway for Pauson-Khand reactions:: Synthesis and reactivity of dicobalt hexacarbonyl complexes of chiral ynamines [J].

Balsells, J ;

Vázquez, J ;

Moyano, A ;

Pericàs, MA ;

Riera, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7291-7302

[2] New Fischer carbene complexes of rhodium(I):: Preparation and 2-cyclopentenone ring synthesis by annelation to alkynes [J].

Barluenga, J ;

Vicente, R ;

López, LA ;

Rubio, E ;

Tomás, M ;

Alvarez-Rúa, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :470-471

[3] 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

[4] [3+2] cycloaddition of Fischer alkenyl carbene complexes to enamines:: An efficient asymmetric approach to cyclopentanoids [J].

Barluenga, J ;

Tomás, M ;

Ballesteros, A ;

Santamaría, J ;

Brillet, C ;

García-Granda, S ;

Piñera-Nicolás, A ;

Vázquez, JT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4516-4517

[5] A new electron-poor Fischer carbene complex:: Unusually efficient and general benzannulation of amino-stabilized alkenyl Fischer carbene complexes [J].

Barluenga, J ;

López, LA ;

Martínez, S ;

Tomás, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7588-7589

[6] Nickel(0)-mediated [2+2+1] cyclization reaction of chromium carbene complexes and internal alkynes [J].

Barluenga, Jose ;

Barrio, Pablo ;

Riesoro, Lorena ;

Lopez, Luis A. ;

Tomas, Miguel .

TETRAHEDRON, 2006, 62 (32) :7547-7551

[7] Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].

Brummond, KM ;

Kent, JL .

TETRAHEDRON, 2000, 56 (21) :3263-3283

[8] CYCLOPENTENONE FORMATION VIA HYDROGEN ACTIVATION IN THE REACTIONS OF CHROMIUM CARBENE COMPLEXES WITH ALKYNES [J].

CHALLENER, CA ;

WULFF, WD ;

ANDERSON, BA ;

CHAMBERLIN, S ;

FARON, KL ;

KIM, OK ;

MURRAY, CK ;

XU, YC ;

YANG, DC ;

DARLING, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1359-1376

[9] CONTRASTERIC REGIOCHEMICAL INCORPORATION OF STANNYLACETYLENES IN THE BENZANNULATION REACTION [J].

CHAMBERLIN, S ;

WATERS, ML ;

WULFF, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3113-3114

[10]

Chung YK, 1999, COORDIN CHEM REV, V188, P297

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