Formal alkyne insertion into alkoxycarbene complexes:: Simple access to enantiopure group 6 alkynyl(alkoxy)carbene complexes

被引：39

作者：

Barluenga, J ^{[1
]}

de la Rúa, RB ^{[1
]}

de Sáa, D ^{[1
]}

Ballesteros, A ^{[1
]}

Tomás, M ^{[1
]}

机构：

[1] Univ Oviedo, CSIC, Inst Quim, Unidad Associada, E-33006 Oviedo, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 31期

关键词：

acetylides; asymmetric synthesis; carbene complexes; cycloaddition; rearrangements;

D O I：

10.1002/anie.200501400

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A single (or iterative) insertion of alkyne units into metal carbene complexes, accompanied by alkoxy exchange, occurs readily to give elusive alkynyl-(alkoxy)carbenes (see scheme) as well as polyalkynyl(alkoxy)carbenes. M = W, Cr, Mo. TMSOTf = trimethylsilyl trifluoromethanesulfonate. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4981 / 4983

页数：3

共 36 条

[21] Electrocatalytic dimerisation of non-heteroatom-substituted manganese alkynylcarbene complexes [J].

Ortin, Y ;

Sournia-Saquet, A ;

Lugan, N ;

Mathieu, R .

CHEMICAL COMMUNICATIONS, 2003, (09) :1060-1061

[22] REARRANGEMENT OF ALKYNYL AND VINYL CARBENOIDS VIA THE RHODIUM(II)-CATALYZED CYCLIZATION REACTION OF ALPHA-DIAZOKETONES [J].

PADWA, A ;

AUSTIN, DJ ;

GAREAU, Y ;

KASSIR, JM ;

XU, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2637-2647

[23] Asymmetric exo-selective Diels-Alder reactions by steric attenuation of secondary orbital interactions [J].

Powers, TS ;

Jiang, WQ ;

Su, J ;

Wulff, WD ;

Waltermire, BE ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6438-6439

[24] ASYMMETRIC ALDOL REACTIONS OF CHIRAL IMIDAZOLIDINONE FISCHER CARBENE COMPLEXES [J].

POWERS, TS ;

SHI, Y ;

WILSON, KJ ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6882-6884

[25] Asymmetric Diels-Alder reactions with chiral acetylenic carbene complexes as dienophiles [J].

Rahm, A ;

Rheingold, AL ;

Wulff, WD .

TETRAHEDRON, 2000, 56 (28) :4951-4965

[26]

RIPOH R, 1993, ORGANOMETALLICS, V12, P2236

[27] Criteria for the elucidation of the pseudopericyclic character of the cyclization of (Z)-1,2,4,6-heptatetraene and its heterosubstituted analogues:: Magnetic properties and natural bond orbital analysis [J].

Rodríguez-Otero, J ;

Cabaleiro-Lago, EM .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (08) :1837-1843

[28] Synthesis and thermal reaction of 1,3-bis(alkylseleno)allenes [J].

Shimizu, T ;

Miyasaka, D ;

Kamigata, N .

ORGANIC LETTERS, 2000, 2 (13) :1923-1925

[29] A new copper-catalyzed [3+2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles [J].

Shintani, R ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10778-10779

[30] Catalytic enantioselective synthesis of β-lactams:: Intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascade [J].

Shintani, R ;

Fu, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (34) :4082-4085

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