Chirons in the 1,3-dioxane series: stereospecific cross-coupling reactions and chirality transfers

被引：4

作者：

Amadji, M

Cahard, D

Moriggi, JD

Toupet, L

Plaquevent, JC ^{[1
]}

机构：

[1] Univ Rouen, Fac Sci, Lab Fonct Azotees & Oxygenees Complexes, IRCOF,UPRESA 6014, F-76821 Mt St Aignan, France

[2] Univ Rennes 1, UMR 6626, Grp Mat Condensee & Mat, F-35042 Rennes, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(98)00171-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium catalyzed cross-coupling reactions are described for enantiopure axially chiral vinylic bromides with arylzinc reagents leading to new compounds with axial chirality. In addition, transfers of axial to central chirality are described. Both reactions exhibit full retention of enantiomeric purity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1657 / 1660

页数：4

共 14 条

[1] First catalytic enantioselective proton abstraction using chiral alkoxides [J].

Amadji, M ;

Vadecard, J ;

Plaquevent, JC ;

Duhamel, L ;

Duhamel, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12483-12484

[2]

AMADJI M, 1995, J CHEM RES-S, P362

[3] 4-PHENYLBENZYLIDENE BENZYLAMINE - A NEW AND CONVENIENT REAGENT FOR THE TITRATION OF SOLUTIONS OF LITHIUM ALKYLS AND METAL AMIDES [J].

DUHAMEL, L ;

PLAQUEVENT, JC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 448 (1-2) :1-3

[4] NICKEL-CATALYZED CROSS-COUPLINGS OF ALKENYL AND ALPHA-METALATED ALKENYL SULFOXIMINES WITH ORGANOMETALLICS - STEREOSELECTIVE SYNTHESIS OF CARBACYCLINS [J].

ERDELMEIER, I ;

GAIS, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1125-1126

[5] TRANSITION-METAL CATALYZED-REACTIONS OF ORGANOZINC REAGENTS [J].

ERDIK, E .

TETRAHEDRON, 1992, 48 (44) :9577-9648

[6] NUCLEAR MAGNETIC RESONANCE AND ULTRAVIOLET SPECTROSCOPY OF SUBSTITUTED AROMATIC ORGANOMETALLIC COMPOUNDS OF LITHIUM MAGNESIUM AND CALCIUM [J].

FRAENKEL, G ;

DAYAGI, S ;

KOBAYASH.S .

JOURNAL OF PHYSICAL CHEMISTRY, 1968, 72 (03) :953-&

[7] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].

KNOCHEL, P ;

SINGER, RD .

CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188

[8] STEREOSELECTIVE SYNTHESIS OF ALKENES AND ALKENYL SULFIDES FROM ALKENYL HALIDES USING PALLADIUM AND RUTHENIUM CATALYSTS [J].

MURAHASHI, SI ;

YAMAMURA, M ;

YANAGISAWA, K ;

MITA, N ;

KONDO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2408-2417

[9] SYNTHESIS OF OLEFINS - CROSS COUPLING OF ALKENYL HALIDES AND GRIGNARD-REAGENTS CATALYZED BY IRON COMPLEXES [J].

NEUMANN, SM ;

KOCHI, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :599-606

[10] VINYLATION OF GRIGNARD REAGENTS - CATALYSIS BY IRON [J].

TAMURA, M ;

KOCHI, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (06) :1487-&

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