Gold(I)-Catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes

被引：86

作者：

Dai, Lun-Zhi ^{[1
]}

Qi, Ming-Juan ^{[1
]}

Shi, Yong-Ling ^{[1
]}

Liu, Xu-Guang ^{[1
]}

Shi, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 16期

关键词：

D O I：

10.1021/ol0713640

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by gold(I). This procedure involves a domino three-membered ring-opening, 6-exo-cycloisomerization, and subsequent intra- or intermolecular nucleophilic addition to a double-bond sequence.

引用

页码：3191 / 3194

页数：4

共 54 条

[1] Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].

Antoniotti, S ;

Genin, E ;

Michelet, V ;

Genêt, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977

[2] Recent applications of gold catalysis in organic synthesis [J].

Arcadi, A ;

Di Giuseppe, S .

CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812

[3] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC LETTERS, 2006, 8 (20) :4489-4492

[4] Efficient gold-catalyzed hydroamination of 1,3-dienes [J].

Brouwer, C ;

He, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1744-1747

[5] STEREOELECTRONIC CONTROL IN ENOLIZATION-KETONIZATION REACTIONS [J].

COREY, EJ ;

SNEEN, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (24) :6269-6278

[6] Catalytic enantioselective Conia-ene reaction [J].

Corkey, BK ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17168-17169

[7]

Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO

[8]

2-A

[9] Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes [J].

Echavarren, AM ;

Nevado, C .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :431-436

[10] Gold-catalyzed intramolecular reaction of indoles with alkynes: Facile formation of eight-membered rings and an unexpected allenylation [J].

Ferrer, C ;

Echavarren, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1105-1109

← 1 2 3 4 5 6 →