A facile synthesis of 3-allyl-4-hydrazinocyclopentenes by the palladium/Lewis acid mediated ring opening of bicyclic hydrazines with allyltributyltin and allyltrimethylsilane

被引：32

作者：

Sajisha, VS ^{[1
]}

Smitha, M ^{[1
]}

Anas, S ^{[1
]}

Radhakrishnan, KV ^{[1
]}

机构：

[1] CSIR, Reg Res Lab, Organ Chem Sect, Div Chem Sci, Trivandrum 695019, Kerala, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

bicyclic hydrazines; disubstituted cyclopentanes; bmim]PF6; allyltri-n-butyltin; Lewis acids; palladium catalyst;

D O I：

10.1016/j.tet.2006.02.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method for the synthesis of 3-allyl-4-hydrazinocyclopentenes from bicyclic hydrazines by the Pd/Lewis acid catalyzed reaction of allyhributyltin and allyltrimethylsilane is described. The role of ionic liquid [bmim]PF6 as a solvent as well as a promoter is also demonstrated by carrying out the reactions in ionic liquid without Lewis acid. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3997 / 4002

页数：6

共 48 条

[1] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[2] Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors [J].

Bournaud, C ;

Robic, D ;

Bonin, M ;

Micouin, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3316-3317

[3] DIRECT, STEREOCONTROLLED TOTAL SYNTHESIS OF 9,11-AZO ANALOG OF PROSTAGLANDIN ENDOPEROXIDE, PGH2 [J].

COREY, EJ ;

NARASAKA, K ;

SHIBASAKI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (20) :6417-6418

[4] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[5]

Diels O, 1925, LIEBIGS ANN CHEM, V443, P242

[6] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[7] Ionic liquids. Green solvents for the future [J].

Earle, MJ ;

Seddon, KR .

PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1391-1398

[8] New developments in catalysis using ionic liquids [J].

Gordon, CM .

APPLIED CATALYSIS A-GENERAL, 2001, 222 (1-2) :101-117

[9] ASYMMETRIC DIELS-ALDER REACTIONS .1. DIASTEREOFACIAL REACTIVITY OF (E)-3-TRIMETHYLSILYLOXYBUTA-1,3-DIENYL 2,3,4,6-TETRA-0-ACETYL-BETA-D-GLUCOPYRANOSIDE TOWARDS CYCLIC DIENOPHILES [J].

GUPTA, RC ;

RAYNOR, CM ;

STOODLEY, RJ ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1773-1785

[10]

HALLBERG A, 1993, CHEM LETT, P1982

← 1 2 3 4 5 →