Highly Efficient and Tunable Synthesis of Dioxabicyclo[4.2.1] Ketals and Tetrahydropyrans via Gold-Catalyzed Cycloisomerization of 2-Alkynyl-1,5-diols

被引：32

作者：

Liu, Le-Ping ^{[1
]}

Hammond, Gerald B. ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

基金：

美国国家科学基金会;

关键词：

NATURAL-PRODUCTS; INDOLE ALKALOIDS; BICYCLIC KETALS; ALDOL REACTION; ACCESS; ALKYNES; ALLENOATES; HYDROALKOXYLATION; CYCLOADDITION; CYCLIZATION;

D O I：

10.1021/ol902215n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diol (1) to dioxabicyclo[4.2.1] ketal (2) and its further transformation to tetrahydropyran (3) are reported. The diol is readily obtained by the reduction of 2-alkynyl-substituted glutarates, isolated from the Michael addition of allenoates to methyl acrylate. These reactions proceeded smoothly under very mild conditions. A plausible mechanism for the formation of the said tetrahydropyran from the corresponding ketal is proposed.

引用

页码：5090 / 5092

页数：3

共 49 条

[1] Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols
Antoniotti, S
Genin, E
Michelet, V
Genêt, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9976 - 9977
[2] Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals
Aponick, Aaron
Li, Chuan-Ying
Palmes, Jean A.
[J]. ORGANIC LETTERS, 2009, 11 (01) : 121 - 124
[3] TBAF-Mediated Aldol Reaction of β-Allenoates: Regio- and Stereoselective Synthesis of (2E,4E)-4-Carbinol Alkadienoates
Aponte, Jose C.
Hammond, Gerald B.
Xu, Bo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4623 - 4625
[4] Alternative synthetic methods through new developments in catalysis by gold
Arcadi, Antonio
[J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3266 - 3325
[5] Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines
Barluenga, Jose
Fernandez-Rodriguez, Manuel Angel
Garcia-Garcia, Patricia
Aguilar, Enrique
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) : 2764 - +
[6] Bartlett P.A., 2006, EXPLOITING CHEM DIVE
[7] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols
Belting, Volker
Krause, Norbert
[J]. ORGANIC LETTERS, 2006, 8 (20) : 4489 - 4492
[8] Golden opportunities in stereoselective catalysis
Bongers, Nadine
Krause, Norbert
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2178 - 2181
[9] Strategies for the formation of tetrahydropyran rings in the synthesis of natural products
Clarke, Paul A.
Santos, Soraia
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) : 2045 - 2053
[10] Gold(I)-Catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes
Dai, Lun-Zhi
Qi, Ming-Juan
Shi, Yong-Ling
Liu, Xu-Guang
Shi, Min
[J]. ORGANIC LETTERS, 2007, 9 (16) : 3191 - 3194

← 1 2 3 4 5 →