PALLADIUM(0) CATALYZED AND NICKEL(0) CATALYZED METALLO-ENE-TYPE CYCLIZATIONS - STEREODIRECTING RESIDENT CHIRALITY

被引：34

作者：

OPPOLZER, W

KELLER, TH

KUO, DL

PACHINGER, W

机构：

[1] Département de Chimie Organique, Université de Genéve

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)88781-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trans-cyclization products were selectively formed from C-6-substituted acetoxy-octadienes only via Ni(0) catalysis (1 → 2) and from C-4-substituted analogs under Pd(0)- and Ni(0) catalysis (7, 8 → 9). C-5-Substituted precursors gave mixtures of diastereoisomers. Nickel(0) catalyzed allylation/methoxycarbonylation of iodo diene 11 afforded 2-oxa-bicyclo[3.3.0]octanone 12 with highly diastereoselective generation of three stereogenic centers. © 1990.

引用

页码：1265 / 1268

页数：4

共 13 条

[1] PALLADIUM-CATALYZED INTRAMOLECULAR ASYMMETRIC ENE REACTIONS OF CHIRAL ALLYLIC SULFONES VIA CHIRAL ALLYLIC SULFINATE-SULFONE REARRANGEMENTS
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[2] METAL-PROMOTED CYCLIZATION .24. SYNTHESIS OF CYCLOPENTANOL DERIVATIVES VIA PALLADIUM-CATALYZED CYCLIC ALLYLMETALLATION-DEHYDROMETALLATION
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[J]. TETRAHEDRON LETTERS, 1989, 30 (03) : 291 - 294
[3] PALLADIUM-CATALYZED INTRAMOLECULAR OLEFIN ALLYLATIONS - STEREOCONTROLLED SYNTHESES OF BICYCLIC SYSTEMS AND EVIDENCE FOR AN ALLYLPALLADIUM OLEFIN-CIS-INSERTION
OPPOLZER, W
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[J]. TETRAHEDRON LETTERS, 1988, 29 (37) : 4705 - 4708
[4] ENANTIOSELECTIVE SYNTHESES OF (+)-ALPHA-SKYTANTHINE, (+)-DELTA-SKYTANTHINE AND (+)-IRIDOMYRMECIN BY AN INTRAMOLECULAR MAGNESIUM-ENE REACTION
OPPOLZER, W
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[J]. TETRAHEDRON LETTERS, 1986, 27 (10) : 1141 - 1144
[5] NICKEL-CATALYZED INTRAMOLECULAR ALLYLATION OF ALKENES AND ALKYNES COUPLED WITH BETA-ELIMINATION OR CARBONYLATION
OPPOLZER, W
BEDOYAZURITA, M
SWITZER, CY
[J]. TETRAHEDRON LETTERS, 1988, 29 (49) : 6433 - 6436
[6] SYNTHESIS OF NITROGEN-CONTAINING OR OXYGEN-CONTAINING RING-SYSTEMS BY PALLADIUM-CATALYZED INTRAMOLECULAR OLEFIN ALLYLATIONS
OPPOLZER, W
GAUDIN, JM
BEDOYAZURITA, M
HUESORODRIGUEZ, J
RAYNHAM, TM
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[J]. TETRAHEDRON LETTERS, 1988, 29 (37) : 4709 - 4712
[7] CATALYTIC INTRAMOLECULAR PALLADIUM-ENE REACTIONS - PRELIMINARY COMMUNICATION
OPPOLZER, W
GAUDIN, JM
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (06) : 1477 - 1481
[8] DIASTEREOCONTROLLED NICKEL(0) CATALYZED AND PALLADIUM(0) CATALYZED METALLO-ENE-TYPE CYCLIZATIONS CARBONYLATIONS
OPPOLZER, W
KELLER, TH
BEDOYAZURITA, M
STONE, C
[J]. TETRAHEDRON LETTERS, 1989, 30 (43) : 5883 - 5886
[9] INTRAMOLECULAR, STOICHIOMETRIC (LI, MG, ZN) AND CATALYTIC (NI, PD, PT) METALLO-ENE REACTIONS IN ORGANIC-SYNTHESIS
OPPOLZER, W
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01): : 38 - 52
[10] PALLADIUM(0)-CATALYZED CYCLIZATIONS OF SIMPLE 1-ARYL-1,7-OCTADIEN-3-YL ACETATES
OPPOLZER, W
SWENSON, RE
PACHINGER, W
[J]. HELVETICA CHIMICA ACTA, 1989, 72 (01) : 14 - 16

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