Synthesis of phosphorus mono- and bicycles by catalytic ring-closing metathesis

被引：59

作者：

Timmer, MSM ^{[1
]}

Ovaa, H ^{[1
]}

Filippov, DV ^{[1
]}

van der Marel, GA ^{[1
]}

van Boom, JH ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 46期

关键词：

regioselectivity; tandem yne-diene metathesis; ethynylphosphonates; phosphane-borane complexes;

D O I：

10.1016/S0040-4039(01)01740-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile route of synthesis of phosphorus oxide and phosphorus borane templates starting from the bifunctional phosphorylating agent bis(diisopropylamino)ethynyiphosphine is presented. Ring-closing enyne metathesis using 4,5-dihydro-imidazol-2-ylidene ruthenium benzylidene complex 3 on these types of substrates led to the formation of mono- and bicyclic phosphorus heterocycles. (C) 2001 Elsvier Science Ltd. All rights reserved.

引用

页码：8231 / 8233

页数：3

共 21 条

[1] A highly efficient and practical synthesis of cyclic phosphinates using ring-closing metathesis [J].

Bujard, M ;

Gouverneur, V ;

Mioskowski, C .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :2119-2123

[2]

Chatterjee AK, 2001, SYNLETT, P1034

[3] CYCLIC PHOSPHONATE ANALOGS OF HEXOPYRANOSES [J].

DARROW, JW ;

DRUECKHAMMER, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :2976-2985

[4]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[5] SYNTHESIS OF CARBOHYDRATE PHOSTONES AS POTENTIAL GLYCOMIMETICS [J].

HANESSIAN, S ;

GALEOTTI, N ;

ROSEN, P ;

OLIVA, G ;

BABU, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (23) :2763-2768

[6] Ring-closing metathesis strategy to P-heterocycles [J].

Hanson, PR ;

Stoianova, DS .

TETRAHEDRON LETTERS, 1999, 40 (17) :3297-3300

[7] Ring closing metathesis reactions on a phosphonate template [J].

Hanson, PR ;

Stoianova, DS .

TETRAHEDRON LETTERS, 1998, 39 (23) :3939-3942

[8] Ring-closing olefin metathesis for the synthesis of phosphorus containing heterocycles [J].

Hetherington, L ;

Greedy, B ;

Gouverneur, V .

TETRAHEDRON, 2000, 56 (14) :2053-2060

[9] METATHESIS OF PHOSPHORUS-CONTAINING OLEFINS CATALYZED BY A CYCLOMETALATED ARYLOXO(CHLORO)NEOPENTYLIDENE-TUNGSTEN COMPLEX [J].

LECONTE, M ;

JOURDAN, I ;

PAGANO, S ;

LEFEBVRE, F ;

BASSET, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) :857-858

[10] An olefin cross-metathesis approach to vinylphosphonate-linked nucleic acids [J].

Lera, M ;

Hayes, CJ .

ORGANIC LETTERS, 2001, 3 (17) :2765-2768

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