The first metal-catalyzed intramolecular [5+2] cycloadditions of vinylcyclopropanes and alkenes: Scope, stereochemistry, and asymmetric catalysis

被引：100

作者：

Wender, PA ^{[1
]}

Husfeld, CO ^{[1
]}

Langkopf, E ^{[1
]}

Love, JA ^{[1
]}

Pleuss, N ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 25期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(98)00355-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first studies of the metal-catalyzed [5+2] cycloadditions of vinylcyclopropanes and alkenes are described. These reactions proceed with exceptional diastereoselectivity and in good to excellent yields. The effect of tether and substituent variations are examined. In addition, preliminary studies show that enantioselective cycloadditions can be achieved through the use of catalysts modified with chiral phosphine ligands. This novel, general, and efficient procedure provides a fundamentally new approach to the synthesis of a variety of products of structural and medicinal significance. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7203 / 7220

页数：18

共 45 条

[1] First studies of the transition metal-catalyzed [5+2] cycloadditions of alkenes and vinylcyclopropanes: Scope and stereochemistry
Wender, PA
Husfeld, CO
Langkopf, E
Love, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) : 1940 - 1941
[2] The first intermolecular transition metal-catalyzed [5+2] cycloadditions with simple, unactivated, vinylcyclopropanes
Wender, PA
Barzilay, CM
Dyckman, AJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (01) : 179 - 180
[3] Transition metal-catalyzed [5+2] cycloadditions: The first studies of asymmetric induction, stereochemistry, and substituent effects
Wender, PA
Husfeld, CO
Kadereit, D
Langkopf, E
Love, JA
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 53 - ORGN
[4] Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes
Wegner, HA
de Meijere, A
Wender, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) : 6530 - 6531
[5] Transition metal-catalyzed [5+2] cycloadditions of allenes and vinylcyclopropanes: First studies of endo-exo selectivity, chemoselectivity, relative stereochemistry, and chirality transfer
Wender, PA
Glorius, F
Husfeld, CO
Langkopf, E
Love, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (22) : 5348 - 5349
[6] Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity
Wender, PA
Dyckman, AJ
[J]. ORGANIC LETTERS, 1999, 1 (13) : 2089 - 2092
[7] Mechanistic understanding of [Rh(NHC)]-catalyzed intramolecular [5+2] cycloadditions of vinyloxiranes and vinylcyclopropanes with alkynes
Zhou, Huan
Wu, Botao
Ma, Jun-An
Dang, Yanfeng
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4295 - 4303
[8] Propargyltrimethylsilanes as Allene Equivalents in Transition Metal-Catalyzed [5+2] Cycloadditions
Wender, Paul A.
Inagaki, Fuyuhiko
Pfaffenbach, Magnus
Stevens, Matthew C.
[J]. ORGANIC LETTERS, 2014, 16 (11) : 2923 - 2925
[9] Rhodium-catalyzed [5+2] cycloadditions of allenes and vinylcyclopropanes: Asymmetric total synthesis of (+)-dictamnol
Wender, PA
Fuji, M
Husfeld, CO
Love, JA
[J]. ORGANIC LETTERS, 1999, 1 (01) : 137 - 139
[10] Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes
Melcher, Michaela-Christina
von Wachenfeldt, Henrik
Sundin, Anders
Strand, Daniel
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (02) : 531 - 535

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