Cyclization/hydrosilylation of functionalized 1,7-dienes to form substituted six-membered carbocycles.

被引：41

作者：

Stengone, CN ^{[1
]}

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

关键词：

catalysis; cyclization; dienes; palladium;

D O I：

10.1016/S0040-4039(99)00022-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cationic palladium complex (phen)Pd(Me)(OEt2)(+) BAr4- [phen = I,10-phenanthroline; Ar = 3,5-C6H3(CF3)(2)] catalyzed the cyclization/hydrosilylation of functionalized 1,7-dienes to form silylated cyclohexanes in good yield and with moderate to good trans-selectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1451 / 1454

页数：4

相关论文

共 15 条

[1] PALLADIUM-CATALYZED AND RHODIUM-CATALYZED CYCLIZATION OF 1,6-DIENES, 1,7-DIENES AND 1,8-DIENES TO CYCLOPENTENES AND METHYLENECYCLOPENTENES - CRYSTAL-STRUCTURE OF DICHLORO(4,4-DIACETYLHEPTA-1,6-DIENE)PLATINUM(II) [J].

GRIGG, R ;

MALONE, JF ;

MITCHELL, TRB ;

RAMASUBBU, A ;

SCOTT, RM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1745-1754

[2] Sequential cyclization/silylation of enynes catalyzed by an organoyttrium complex [J].

Molander, GA ;

Retsch, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :8817-8825

[3] Catalytic cyclization/silylation of dienes containing 1,1-disubstituted olefins using organolanthanide and group 3 organometallic complexes [J].

Molander, GA ;

Dowdy, ED ;

Schumann, H .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3386-3396

[4] Stereoselective synthesis of carbobicyclics via organoyttrium-catalyzed sequential cyclization/silylation reactions [J].

Molander, GA ;

Nichols, PJ ;

Noll, BC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2292-2306

[5] ORGANOYTTRIUM-CATALYZED SEQUENTIAL CYCLIZATION SILYLATION REACTIONS OF 1,5-DIENES AND 1,6-DIENES [J].

MOLANDER, GA ;

NICHOLS, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4415-4416

[6] Silylcarbocyclizations of 1,6-diynes [J].

Ojima, I ;

Zhu, JW ;

Vidal, ES ;

Kass, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (27) :6690-6697

[7] SILYLCARBOCYCLIZATION REACTIONS CATALYZED BY RH AND RH-CO COMPLEXES [J].

OJIMA, I ;

DONOVAN, RJ ;

SHAY, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6580-6582

[8] HYDROSILATION OF DIENES CATALYZED BY CP-ASTERISK-2NDCH(SIME(3))(2) [J].

ONOZAWA, S ;

SAKAKURA, T ;

TANAKA, M .

TETRAHEDRON LETTERS, 1994, 35 (44) :8177-8180

[9] Palladium-catalyzed borylstannylative carbocyclization of diynes and an enyne compound [J].

Onozawa, S ;

Hatanaka, Y ;

Choi, N ;

Tanaka, M .

ORGANOMETALLICS, 1997, 16 (25) :5389-5391

[10] Electronic effects on the beta-alkyl migratory insertion reaction of para-substituted styrene methyl palladium complexes [J].

Rix, FC ;

Brookhart, M ;

White, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2436-2448