Gold-catalyzed hydroarylation of allenes: A highly regioselective carbon-carbon bond formation producing six-membered rings

被引：117

作者：

Watanabe, Toshiaki ^{[1
]}

Oishi, Shinya ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 23期

关键词：

D O I：

10.1021/ol702179n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed intramolecular hydroarylation of allenic anilines and phenols offers an efficient route to dihydroquinoline and chromene derivatives under mild reaction conditions. The hydroarylation takes place at the terminal or central allenic carbon depending on the substrate structure, leading to a highly selective formation of six-membered rings.

引用

页码：4821 / 4824

页数：4

共 53 条

[1] MERCURY(II) TRIFLUOROACETATE-MEDIATED CYCLIZATION OF ARYL ALLENIC ETHERS [J].

BALASUBRAMANIAN, T ;

BALASUBRAMANIAN, KK .

TETRAHEDRON LETTERS, 1991, 32 (45) :6641-6644

[2] Nucleophilic transition metal based cyclization of allenes [J].

Bates, RW ;

Satcharoen, V .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21

[3] Sequential N-acylamide methylenation-enamide ring-closing metathesis:: Construction of benzo-fused nitrogen heterocycles [J].

Bennasar, M. Lluisa ;

Roca, Tomas ;

Monerris, Manuel ;

Garcia-Diaz, Davinia .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :7028-7034

[4] Synthesis of 2,3-dihydropyridines, cyclobutanopyrrolines and quinolines from lithiated allenes and isothiocyanates [J].

Brandsma, L ;

Nedolya, NA ;

Verkruijsse, HD ;

Owen, NL ;

Li, D ;

Trofimov, BA .

TETRAHEDRON LETTERS, 1997, 38 (39) :6905-6908

[5] REGIOSPECIFIC ALKENYLATION OF PHENOLS BY 1,1-DIMETHYLALLENE PROMOTED BY PLATINUM CATALYSTS [J].

DERENZI, A ;

PANUNZI, A ;

SAPORITO, A ;

VITAGLIANO, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (07) :993-996

[6] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[7] Golden times for allenes:: Gold-catalyzed cycloisomerization of β-hydroxyallenes to dihydropyrans [J].

Gockel, Birgit ;

Krause, Norbert .

ORGANIC LETTERS, 2006, 8 (20) :4485-4488

[8] Relativistic effects in homogeneous gold catalysis [J].

Gorin, David J. ;

Toste, F. Dean .

NATURE, 2007, 446 (7134) :395-403

[9] Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridino[5,6-g]quinolines [J].

Hamann, LG ;

Higuchi, RI ;

Zhi, L ;

Edwards, JP ;

Wang, XN ;

Marschke, KB ;

Kong, JW ;

Farmer, LJ ;

Jones, TK .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (04) :623-639

[10] Enantioselective synthesis of chromenes [J].

Hardouin, C ;

Burgaud, L ;

Valleix, A ;

Doris, E .

TETRAHEDRON LETTERS, 2003, 44 (03) :435-437

← 1 2 3 4 5 6 →