CHELATION-CONTROLLED CHEMO-SELECTIVE, REGIO-SELECTIVE AND ENANTIO-SELECTIVE SYNTHESIS OF HOMOALLYLIC ALCOHOLS

被引：25

作者：

CALO, V ^{[1
]}

FIANDANESE, V ^{[1
]}

NACCI, A ^{[1
]}

SCILIMATI, A ^{[1
]}

机构：

[1] UNIV BARI,DIPARTIMENTO FARMACOCHIM,I-70125 BARI,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)85251-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active allylic sulphides 10-13. bearing two different leaving groups, react with organocopper reagents by selective substitution of the heterocycle moiety leading to optically active homoallylic pivalates with chemo-, regio- and enantio-control. This selectivity seems to be related to the coordination exerted by the heterocyclic nucleus towards the organometal.

引用

收藏

页码：7283 / 7292

页数：10

相关论文

共 26 条

[1] A DUAL REGIOCONTROL IN THE COPPER-CATALYZED GRIGNARD REACTION WITH PRIMARY ALLYLIC ACETATES [J].

BACKVALL, JE ;

SELLEN, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (11) :827-829

[2]

BACKVALL JE, 1990, J AM CHEM SOC, V112, P6615

[3] MODEL SYSTEMS FOR TYPE-I COPPER PROTEINS - STRUCTURES OF COPPER COORDINATION-COMPOUNDS WITH THIOETHER AND AZOLE-CONTAINING LIGANDS [J].

BOUWMAN, E ;

DRIESSEN, WL ;

REEDIJK, J .

COORDINATION CHEMISTRY REVIEWS, 1990, 104 (01) :143-172

[4] REGIOSELECTIVE ALPHA-ADDITION OF ORGANOCOPPER REAGENTS TO GAMMA-(BENZOTHIAZOLE-2-THIO)-ALPHA,BETA-ENOATES GOVERNED BY ANCHIMERIC COORDINATION - SYNTHESIS OF ALPHA-ALKYLATED-BETA,GAMMA-ENOATES [J].

CALO, V ;

LOPEZ, L ;

PESCE, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (16) :1252-1253

[5] SELECTIVITY IN ALLYLIC SUBSTITUTIONS WITH ORGANOMETALLICS THROUGH NEIGHBORING COORDINATION - SYNTHESIS AND REACTIONS OF COPPER(I) PI-COMPLEXES WITH 2-ALLYLOXYBENZOTHIAZOLES [J].

CALO, V ;

LOPEZ, L ;

PESCE, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 231 (02) :179-183

[6] REGIOCONTROL BY ANCHIMERIC COORDINATION IN THE REACTIONS OF ORGANOCOPPER REAGENTS WITH ALLYLIC SUBSTRATES BEARING 2 LEAVING GROUPS - SYNTHESIS OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS [J].

CALO, V ;

DENITTI, C ;

LOPEZ, L ;

SCILIMATI, A .

TETRAHEDRON, 1992, 48 (29) :6051-6058

[7] REGIOREVERSED NUCLEOPHILIC-SUBSTITUTION OF 2-(ALLYLOXY)BENZOTHIAZOLE BY ALLYLIC GRIGNARD-REAGENTS - A REGIOSELECTIVE SYNTHESIS OF 1,5-DIENES [J].

CALO, V ;

LOPEZ, L ;

PESCE, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1301-1304

[8] SELECTIVITY IN ALLYLIC SUBSTITUTIONS WITH ORGANOMETALLICS THROUGH NEIGHBORING COORDINATION .2. REACTIONS OF 2-ALLYLTHIOBENZOTHIAZOLES WITH ORGANOCOPPER REAGENTS [J].

CALO, V ;

LOPEZ, L ;

CARLUCCI, WF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :2953-2956

[9] MECHANISTIC ASPECTS OF REDUCTIONS OF ALLYLIC ETHERS AND ACETATES WITH ORGANOCUPRATES [J].

CLAESSON, A ;

SAHLBERG, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 170 (03) :355-363

[10]

COMMERCONA, 1975, TETRAHEDRON LETT, P3837