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

[11] COPPER(I) CATALYZED-REACTIONS OF ORGANOLITHIUMS AND GRIGNARD-REAGENTS [J].

ERDIK, E .

TETRAHEDRON, 1984, 40 (04) :641-657

[12]

Fouquet G., 1974, ANGEW CHEM, V86, P50

[13] ALKYLATION OF ALLYLIC DERIVATIVES .5. LOSS OF DOUBLE-BOND CONFIGURATION ASSOCIATED WITH ALPHA-ALKYLATION OF ALLYLIC CARBOXYLATES WITH DIALKYLCUPRATES [J].

GOERING, HL ;

KANTNER, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) :721-724

[14] ALKYLATION OF ALLYLIC DERIVATIVES .8. REGIOCHEMISTRY AND STEREOCHEMISTRY OF ALKYLATION OF ALLYLIC CARBOXYLATES WITH LITHIUM METHYLCYANOCUPRATE [J].

GOERING, HL ;

KANTNER, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :422-426

[15] SYNTHESIS USING SULFONES .25. SUBSTITUTION ON SULFONES - THE PHENYLSULFINATE ANION AS A LEAVING GROUP IN THE SUBSTITUTION OF ALLYLIC SULFONES BY GRIGNARD-REAGENTS IN THE PRESENCE OF COPPER-SALTS [J].

JULIA, M ;

RIGHINITAPIE, A ;

VERPEAUX, JN .

TETRAHEDRON, 1983, 39 (20) :3283-3287

[16] The optical rotatory powers of (+)-gamma-methyl-n-heptane [J].

Kenyon, J ;

Platt, BC .

JOURNAL OF THE CHEMICAL SOCIETY, 1939, :633-637

[17] 5-AZA-SEMICORRINS - A NEW CLASS OF BIDENTATE NITROGEN LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].

LEUTENEGGER, U ;

UMBRICHT, G ;

FAHRNI, C ;

VONMATT, P ;

PFALTZ, A .

TETRAHEDRON, 1992, 48 (11) :2143-2156

[18] ORGANOMETAL CHEMISTRY .8. REACTION OF ORGANOCUPRATES WITH ALLYLIC ACETATES - PROBABLE EXISTENCE OF PI-ALLYLIC COPPER-COMPLEXES [J].

LEVISALLES, J ;

RUDLERCHAUVIN, M ;

RUDLER, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 136 (01) :103-110

[19] THE ROLE OF BF3.ET2O IN REACTIONS OF LOWER ORDER (GILMAN) ORGANOCUPRATES [J].

LIPSHUTZ, BH ;

ELLSWORTH, EL ;

SIAHAAN, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1351-1358

[20] NUCLEOPHILIC AND ORGANOMETALLIC DISPLACEMENT-REACTIONS OF ALLYLIC COMPOUNDS - STEREOCHEMISTRY AND REGIOCHEMISTRY [J].

MAGID, RM .

TETRAHEDRON, 1980, 36 (13) :1901-1930