A versatile synthesis of (E)- and (Z)-1-halo-2-(alkoxymethyl)-1,3-butadienes and their condensation with aldehydes

被引：33

作者：

Wong, T ^{[1
]}

Tjepkema, MW ^{[1
]}

Audrain, H ^{[1
]}

Wilson, PD ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 06期

关键词：

D O I：

10.1016/0040-4039(95)02303-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct synthesis of various stereodefined dienes 4-11 from propargyl alcohols upon direct addition of vinylmagnesium chloride and manipulation of the resulting magnesium chelate 3 is described. These halo-dienes provided access to the corresponding dienyllithium reagents which were condensed with the aldehydes 13, 15, 17, and 19 to provide the secondary alcohols 14, 16, 18, 20, and 21, respectively, in a stereoselective manner.

引用

页码：755 / 758

页数：4

共 42 条

[1] A STEREOCONTROLLED INTRAMOLECULAR CYCLOADDITION - SIGMATROPIC REARRANGEMENT APPROACH TO A TRICYCLO[7.4.0/1,6/.0/1,10]TRIDECANE PRECURSOR FOR (+/-) GASCARDIC ACID [J].

BERUBE, G ;

FALLIS, AG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (01) :77-83

[2]

Boa A. N., 1994, Contemp. Org. Syn, V1, P47, DOI [10.1039/co9940100047, DOI 10.1039/CO9940100047]

[3] BROMINATION, DEBROMINATION AND DEBROMOSILYLATION OF SILYLSTYRENES AND OTHER VINYLSILANES [J].

BROOK, AG ;

DUFF, JM ;

REYNOLDS, WF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 121 (03) :293-306

[4] THE DIELS-ALDER ROUTE TO ALLYLSILANES FROM 1-TRIMETHYLSILYLBUTADIENES [J].

CARTER, MJ ;

FLEMING, I ;

PERCIVAL, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2415-2434

[5]

CHAN TH, 1977, TETRAHEDRON LETT, P3317

[6]

CHAN TH, 1979, SYNTHESIS-STUTTGART, P761

[7] CONVENIENT SYNTHESES OF PRECURSORS OF SILYLATED 1,3-DIENES [J].

CHOU, TS ;

TSO, HH ;

TAO, YT ;

LIN, LC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :244-246

[8] ORGANOALUMINUM-PROMOTED CYCLOADDITION OF TRIALKYLSILYLKETENE WITH ALDEHYDES - A NEW, STEREOSELECTIVE APPROACH TO CIS-2-OXETANONES AND 2(Z)-ALKENOIC ACIDS [J].

CONCEPCION, AB ;

MARUOKA, K ;

YAMAMOTO, H .

TETRAHEDRON, 1995, 51 (14) :4011-4020

[9] STEREOSELECTIVE SYNTHESIS OF POLYSUBSTITUTED OLEFINS VIA THE FORMATION OF 1,1-BIMETALLOALKENES [J].

CRETON, I ;

MAREK, I ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1995, 36 (41) :7451-7454

[10]

FALLIS AG, ADV CYCLOADDITION

← 1 2 3 4 5 →