Rhodium-Catalyzed Intermolecular [2+2] Cycloaddition of Terminal Alkynes with Electron-Deficient Alkenes

被引：58

作者：

Sakai, Kazunori ^{[1
]}

Kochi, Takuya ^{[1
]}

Kakiuchi, Fumitoshi ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 05期

关键词：

DIMETHYL ACETYLENEDICARBOXYLATE; CYCLOBUTANE DERIVATIVES; ESTERS; COMPLEXES; VINYLIDENE; NORBORNENES; ALKYLIDENE; PROPIOLATE; REACTIVITY; ENYNES;

D O I：

10.1021/ol303510k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes is reported. The reaction proceeds with an 8-quinolinolato rhodium/phosphine catalyst system to give cyclobutenes from various substrates having polar functional groups in high yields with complete regioselectivity.

引用

页码：1024 / 1027

页数：4

共 57 条

[41] ASYMMETRIC [2 + 2] CYCLOADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT [J].

NARASAKA, K ;

HAYASHI, Y ;

SHIMADZU, H ;

NIIHATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8869-8885

[42] Nickel-Catalyzed Intermolecular [2+2] Cycloaddition of Conjugated Enynes with Alkenes [J].

Nishimura, Akira ;

Ohashi, Masato ;

Ogoshi, Sensuke .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (38) :15692-15695

[43] REACTION OF KETENEALKYLSILYLACETALS WITH ETHYL PROPIOLATE [J].

QUENDO, A ;

ROUSSEAU, G .

TETRAHEDRON LETTERS, 1988, 29 (49) :6443-6446

[44]

Regan A. C., 1995, COMPREHENSIVE ORGANI, V1, P516

[45] CONDENSATION OF PROPIOLIC ESTERS WITH OLEFINS CATALYZED BY THE C5H5FE(CO)2 CATION [J].

ROSENBLUM, M ;

SCHECK, D .

ORGANOMETALLICS, 1982, 1 (02) :397-400

[46] Rhodium-Catalyzed anti-Markovnikov Addition of Secondary Amines to Arylacetylenes at Room Temperature [J].

Sakai, Kazunori ;

Kochi, Takuya ;

Kakiuchi, Fumitoshi .

ORGANIC LETTERS, 2011, 13 (15) :3928-3931

[47] Enantioselective Ficini Reaction: Ruthenium/PNNP-Catalyzed [2+2] Cycloaddition of Ynamides with Cyclic Enones [J].

Schotes, Christoph ;

Mezzetti, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (13) :3072-3074

[48] UBER DIE KATALYTISCHE ANLAGERUNG VON OLEFINEN UND ALKINEN AN NORBORNADIEN MIT NI0-VERBINDUNGEN UND EINEM NEUEN NI2-KOMPLEX [J].

SCHRAUZER, GN ;

GLOCKNER, P .

CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (09) :2451-&

[49] Rh-catalyzed enantioselective [2+2] cycloaddition of alkynyl esters and norbornene derivatives [J].

Shibata, T ;

Takami, K ;

Kawachi, A .

ORGANIC LETTERS, 2006, 8 (07) :1343-1345

[50] LEWIS ACID-CATALYZED REACTIONS OF METHYL PROPIOLATE WITH UNACTIVATED ALKENES [J].

SNIDER, BB ;

RODINI, DJ ;

CONN, RSE ;

SEALFON, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) :5283-5293

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