REGIOSELECTIVE AND ENANTIOSELECTIVE SILANE-TERMINATED INTRAMOLECULAR HECK REACTIONS

被引：88

作者：

TIETZE, LF

SCHIMPF, R

机构：

[1] Institut für Organische Chemie, Universität Göttingen, D-37077

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 10期

关键词：

D O I：

10.1002/anie.199410891

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The selective formation of tertiary sp3 centers is possible when allylsilanes 1 are employed as the alkene component in the title reaction. Application of a chiral catalyst system makes the reaction enantioselective. Primarily hetero‐ and carbo‐cycles 2 arise with the catalyst system [Pd2(dba)3/PPh3/Ag2O]; 3 is the main product with Pd(OAc2)/PPh3/NPr4Br/KOAc. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1089 / 1091

页数：3

相关论文

共 18 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].

ABELMAN, MM ;

OH, T ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133

[2] PALLADIUM PHOSPHINATED POLYSTYRENE AS A CATALYST IN THE HECK ARYLATION - A COMPARATIVE-STUDY [J].

ANDERSSON, CM ;

KARABELAS, K ;

HALLBERG, A ;

ANDERSSON, C .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3891-3895

[3] CATALYTIC ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF PHYSOSTIGMINE - FORMATION OF QUATERNARY CARBON CENTERS WITH HIGH ENANTIOSELECTION BY INTRAMOLECULAR HECK REACTIONS OF (Z)-2-BUTENANILIDES [J].

ASHIMORI, A ;

MATSUURA, T ;

OVERMAN, LE ;

POON, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6949-6951

[4] CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND [J].

ASHIMORI, A ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4571-4572

[5]

BRUNNER H, 1991, SYNTHESIS-STUTTGART, P1121

[6] THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS [J].

GRIGG, R ;

SANTHAKUMAR, V ;

SRIDHARAN, V ;

STEVENSON, P ;

TEASDALE, A ;

THORNTONPETT, M ;

WORAKUN, T .

TETRAHEDRON, 1991, 47 (46) :9703-9720

[7] ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF OPIUM-ALKALOIDS AND MORPHINANS - TOTAL SYNTHESIS OF (-)-DIHYDROCODEINONE AND (+)-DIHYDROCODEINONE AND (-)-MORPHINE AND (+)-MORPHINE [J].

HONG, CY ;

KADO, N ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11028-11029

[8] PALLADIUM-CATALYZED VINYLATION OF ORGANIC HALIDES UNDER SOLID LIQUID-PHASE TRANSFER CONDITIONS [J].

JEFFERY, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1287-1289

[9] HIGHLY STEREOSPECIFIC PALLADIUM-CATALYZED VINYLATION OF VINYLIC HALIDES UNDER SOLID-LIQUID PHASE-TRANSFER CONDITIONS [J].

JEFFERY, T .

TETRAHEDRON LETTERS, 1985, 26 (22) :2667-2670

[10] THE EFFECT OF ADDED SILVER-NITRATE ON THE PALLADIUM-CATALYZED ARYLATION OF ALLYLTRIMETHYLSILANES [J].

KARABELAS, K ;

WESTERLUND, C ;

HALLBERG, A .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3896-3900