Phosphine triggered [3+2] allenoate-acrylate annulation: a mechanistic enlightenment

被引：172

作者：

Mercier, Evan

Fonovic, Branden

Henry, Chris

Kwon, Ohyun ^{[1
]}

Dudding, Travis

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 20期

基金：

美国国家卫生研究院; 加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

D O I：

10.1016/j.tetlet.2007.03.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mechanistic study of phosphine-mediated [3+2] annulation of allenoate and acrylate is presented. The insight gained has identified that (1) [3+2] cycloaddition proceeds through a stepwise mechanism and (2) the involvement of a molecule of water, which services as a proton-shuttle, is essential for annulated product formation. (C) 2007 Elsevier Ltd. All rights reserved.

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页码：3617 / 3620

页数：4

相关论文

共 34 条

[11] REACTION-PATH FOLLOWING IN MASS-WEIGHTED INTERNAL COORDINATES [J].

GONZALEZ, C ;

SCHLEGEL, HB .

JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) :5523-5527

[12] AN IMPROVED ALGORITHM FOR REACTION-PATH FOLLOWING [J].

GONZALEZ, C ;

SCHLEGEL, HB .

JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (04) :2154-2161

[13] A CORRELATION OF REACTION RATES [J].

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :334-338

[14] Phosphine-mediated reductive condensation of γ-acyloxy butynoates:: A diversity oriented strategy for the construction of substituted Furans [J].

Jung, CK ;

Wang, JC ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4118-4119

[15] Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst [J].

Kamijo, S ;

Kanazawa, C ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9260-9266

[16]

KIRMSE W, 1984, J AM CHEM SOC, V106, P1991

[17] Novel phosphine-catalyzed zipper cyclization of aliphatic diyne-dione and yne-dione systems [J].

Kuroda, H ;

Tomita, I ;

Endo, T .

ORGANIC LETTERS, 2003, 5 (02) :129-131

[18] DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY [J].

LEE, CT ;

YANG, WT ;

PARR, RG .

PHYSICAL REVIEW B, 1988, 37 (02) :785-789

[19] Synthetic methodology using tertiary phosphines as nucleophilic catalysts [J].

Lu, XY ;

Du, YS ;

Lu, C .

PURE AND APPLIED CHEMISTRY, 2005, 77 (12) :1985-1990

[20] Reactions of electron-deficient alkynes and allenes under phosphine catalysis [J].

Lu, XY ;

Zhang, CM ;

Xu, ZR .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (07) :535-544

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