A stereoselective synthesis of silylated polyunsaturated halides from α,β-epoxysilanes

被引：15

作者：

Babudri, F ^{[1
]}

Fiandanese, V ^{[1
]}

Marchese, G ^{[1
]}

Punzi, A ^{[1
]}

机构：

[1] Univ Bari, Dipartimento Chim, Ctr CNR Studio Metodol Innovat Sintesi Organ, I-70126 Bari, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 03期

关键词：

silicon and compounds; epoxysilanes; stereoselective synthesis; unsaturated halogenoderivatives;

D O I：

10.1016/S0040-4020(00)01010-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic approach to silylated polyunsaturated halides has been developed, starting from the readily available (1E,3E)-1,4-bis(trimethylsilyl)-1,3-butadiene and (3E)-1,4-bis(trimethylsilyl)-3-buten-1-yne. A simple epoxidation reaction, followed by regioselective cl-opening of the epoxide ring by metal halides affords the corresponding halohydrins with a high degree of stereoselectivity. A subsequent p-elimination reaction from these compounds leads to (Z,E)-dienyl halides and to (Z)-enyne halides. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：549 / 554

页数：6

共 23 条

[1] A NEW STRAIGHTFORWARD AND GENERAL-APPROACH TO DIENAMIDE NATURAL-PRODUCTS [J].

BABUDRI, F ;

FIANDANESE, V ;

NASO, F ;

PUNZI, A .

TETRAHEDRON LETTERS, 1994, 35 (13) :2067-2070

[2] New synthesis of leukotriene B3 methyl ester from bis(trimethylsilyl) unsaturated derivatives [J].

Babudri, F ;

Fiandanese, V ;

Hassan Omar, O ;

Punzi, A ;

Naso, F .

TETRAHEDRON, 1998, 54 (17) :4327-4336

[3]

BABUDRI F, 1995, SYNLETT, P817

[4] CONJUGATED POLYENE SYNTHESIS VIA DISILYL DERIVATIVES - A DIRECT ACCESS TO OSTOPANIC ACID, A PLANT ANTICANCER AGENT, AND TO (6E)-LTB3 LEUKOTRIENE [J].

BABUDRI, F ;

FIANDANESE, V ;

NASO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6245-6248

[5]

BABUDRI F, 1992, SYNLETT, P221

[6] Novel synthetic approach to (S)-coriolic acid [J].

Babudri, F ;

Fiandanese, V ;

Marchese, G ;

Punzi, A .

TETRAHEDRON, 2000, 56 (02) :327-331

[7] A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES [J].

BAJWA, JS ;

ANDERSON, RC .

TETRAHEDRON LETTERS, 1991, 32 (26) :3021-3024

[8]

BASSINDALE AR, 1995, B SOC CHIM FR, V132, P604

[9] Lewis acid mediated ring opening of propargylic epoxides: A stereospecific synthesis of 1,2-disubstituted homopropargylic alcohols [J].

Bernard, N ;

Chemla, F ;

Normant, JF .

TETRAHEDRON LETTERS, 1998, 39 (37) :6715-6718

[10] A stereospecific synthesis of bromoallenols from propargylic epoxides. [J].

Bernard, N ;

Chemla, F ;

Normant, JF .

TETRAHEDRON LETTERS, 1998, 39 (48) :8837-8840

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