Synthesis of 1,1-dibromo-1-alkenes from partially and unprotected aldoses

被引：24

作者：

Dolhem, F ^{[1
]}

Lièvre, C ^{[1
]}

Demailly, G ^{[1
]}

机构：

[1] Univ Picardie, Lab Chim Glucides, F-80039 Amiens, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期

关键词：

dibromoalkenes; aldoses; dibromomethyltriphenylphosphonium bromide; ylid;

D O I：

10.1016/S0040-4039(02)00149-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Partially and unprotected aldoses react with dibromomethylenetriphenylphosphorane. generated in situ from dibromomethyltriphenylphosphonium bromide in the presence of zinc, to give corresponding unsaturated Wittig adducts in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1847 / 1849

页数：3

共 13 条

[1] A CONVENIENT PROCEDURE FOR THE PREPARATION OF REACTIVE ZINC FOR THE REFORMATSKY REACTION [J].

BOUHLEL, E ;

RATHKE, MW .

SYNTHETIC COMMUNICATIONS, 1991, 21 (01) :133-136

[2]

Corey E.J., 1972, TETRAHEDRON LETT, V13, P3769, DOI DOI 10.1016/S0040-4039(01)94157-7

[3] COMPLETELY SPIROCYCLOPROPANATED MACROCYCLIC OLIGODIACETYLENES - THE FAMILY OF EXPLODING [N]ROTANES [J].

DEMEIJERE, A ;

KOZHUSHKOV, S ;

HAUMANN, T ;

BOESE, R ;

PULS, C ;

COONEY, MJ ;

SCOTT, LT .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (02) :124-131

[4] Facile dibromoolefination of lactones using bromomethylenetriphenylphosphorane [J].

Lakhrissi, Y ;

Taillefumier, C ;

Chrétien, F ;

Chapleur, Y .

TETRAHEDRON LETTERS, 2001, 42 (41) :7265-7268

[5] Wittig-type reaction on unprotected aldoses -: Synthesis of α,β-unsaturated esters [J].

Le Mignot, V ;

Lièvre, C ;

Fréchou, C ;

Demailly, G .

TETRAHEDRON LETTERS, 1998, 39 (09) :983-984

[6] WITTIG-TYPE REACTIONS WITH PARTIALLY PROTECTED ALDOSES - SYNTHESIS OF ACYCLIC ALDOOCTENOATES AND OCTENONITRILES WITH E-STEREOCHEMISTRY [J].

LIEVRE, C ;

FRECHOU, C ;

DEMAILLY, G .

TETRAHEDRON LETTERS, 1995, 36 (36) :6467-6470

[7] Reaction of partially protected aldoses with stabilized arsenic ylides: Synthesis of E unsaturated acyclic derivatives and C-glycosyl derivatives [J].

Lievre, C ;

Frechou, C ;

Demailly, G .

CARBOHYDRATE RESEARCH, 1997, 303 (01) :1-15

[8] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].

MARYANOFF, BE ;

REITZ, AB .

CHEMICAL REVIEWS, 1989, 89 (04) :863-927

[9] A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes [J].

Michel, P ;

Gennet, D ;

Rassat, A .

TETRAHEDRON LETTERS, 1999, 40 (49) :8575-8578

[10] NEW SYNTHESIS OF 1,1-DIBROMOOLEFINS VIA PHOSPHINE-DIBROMOMETHYLENES - REACTION OF TRIPHENYLPHOSPHINE WITH CARBON TETRABROMIDE [J].

RAMIREZ, F ;

MCKELVIE, N ;

DESAI, NB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (09) :1745-&

← 1 2 →