Metal-catalyzed regioselective oxy-functionalization of internal alkynes: An entry into ketones, acetals, and spiroketals

被引：210

作者：

Liu, Bo ^{[1
]}

De Brabander, Jef K. ^{[1
]}

机构：

[1] Univ Texas, SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol0619819

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Platinum(II) and an unusual cationic gold( I) complex were identified as mild catalysts for the room temperature cycloisomerization or tandem hydroalkoxylation/acetal formation of unactivated internal alkynols. Under the appropriate conditions, 5-endo, 5-exo, 6-endo, and 6-exo cycloisomerization modes are all available.

引用

页码：4907 / 4910

页数：4

共 26 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] 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

[3] Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions [J].

Barluenga, J ;

Diéguez, A ;

Fernández, A ;

Rodríguez, F ;

Fañanás, FJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) :2091-2093

[4] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[5] Cyclisation of acetylenic carboxylic acids and acetylenic alcohols to oxygen-containing heterocycles using cationic rhodium(I) complexes [J].

Elgafi, S ;

Field, LD ;

Messerle, BA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :97-104

[6] EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST [J].

FUKUDA, Y ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3729-3731

[7] An IrI-catalyzed exo-selective tandem cycloisomerization/hydroalkoxylation of bis-homopropargylic alcohols at room temperature [J].

Genin, E ;

Antoniotti, S ;

Michelet, V ;

Genet, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) :4949-4953

[8] Platinum(II)-catalyzed addition of alcohols to alkynes [J].

Hartman, JW ;

Sperry, L .

TETRAHEDRON LETTERS, 2004, 45 (19) :3787-3788

[9]

Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO

[10]

2-F

← 1 2 3 →