STEREOCONTROLLED OXASPIROCYCLIZATION OF CONJUGATED DIENES VIA PALLADIUM CATALYSIS

被引:0
|
作者
BACKVALL, JE
ANDERSSON, PG
机构
来源
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mild palladium-catalyzed spirocyclizations of 1-(3-hydroxyalkyl)- and 1-(4-hydroxyalkyl)-1,3-cycloalkadienes (5a, 5b, 5d, and 5e) have been developed. The reactions proceed via a spirocyclic pi-(allyl)palladium intermediate and result in the 1,4-addition of the hydroxy function and a chloride or an acetate. The stereochemistry of the reactions can be controlled to give either cis or trans 1,4-addition across the double bond.
引用
收藏
页码:2274 / 2276
页数:3
相关论文
共 50 条
  • [21] Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones
    Jiang, Huanfeng
    He, Li
    Li, Xianwei
    Chen, Huoji
    Wu, Wanqing
    Fu, Wei
    CHEMICAL COMMUNICATIONS, 2013, 49 (80) : 9218 - 9220
  • [22] Highly regioselective thiocarbonylation of conjugated dienes via palladium-catalyzed three-component coupling reactions
    Xiao, WJ
    Vasapollo, G
    Alper, H
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13): : 4138 - 4144
  • [23] REGIOCONTROLLED AND STEREOCONTROLLED C-C BOND FORMATION VIA LINEAR DIMERIZATION OF CONJUGATED DIENES CATALYZED BY NICKEL-AMINOPHOSPHINITE COMPLEXES
    DENIS, P
    JEAN, A
    CRCIZY, JF
    MORTREUX, A
    PETIT, F
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) : 1292 - 1294
  • [24] NEW CYCLIZATION REACTION OF CONJUGATED DIENES WITH ISOCYANATE CATALYSED BY PALLADIUM COMPLEXES
    OHNO, K
    TSUJI, J
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (06): : 247 - &
  • [25] INSERTION REACTIONS OF CONJUGATED DIENES WITH PI-ALLYLIC PALLADIUM COMPLEXES
    TAKAHASH.Y
    SAKAI, S
    ISHII, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 16 (01) : 177 - &
  • [26] The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes
    Binns, F
    Hayes, R
    Hodgetts, KJ
    Saengchantara, ST
    Wallace, TW
    Wallis, CJ
    TETRAHEDRON, 1996, 52 (10) : 3631 - 3658
  • [27] Highly regio- A nd stereoselective synthesis of bis-sulfanyl substituted conjugated dienes by copper-palladium cooperative catalysis
    Li, Yuan
    Wu, Jin
    Li, Hui
    Sun, Qian
    Xiong, Lixue
    Yin, Guodong
    Organic Chemistry Frontiers, 2021, 8 (03) : 628 - 634
  • [28] Hybrid Palladium-Catalyzed Intramolecular Carboamination of Conjugated Dienes: Synthesis of Functionalized Pyrrolidines via Selective Trifluoromethylarene Defluorination
    Zhang, Feijie
    Zhang, Guocong
    Zhou, Qixin
    Bian, Tiancen
    Zhou, Liejin
    Zhang, Zuxiao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7790 - 7794
  • [29] Selective 1,4-syn-Addition to Cyclic 1,3-Dienes via Hybrid Palladium Catalysis
    Liang, Yan
    Bian, Tiancen
    Yadav, Komal
    Zhou, Qixin
    Zhou, Liejin
    Sun, Rui
    Zhang, Zuxiao
    ACS CENTRAL SCIENCE, 2024, 10 (06) : 1191 - 1200
  • [30] CYCLODIMERIZATION OF CONJUGATED DIENES IN A HOMOGENOUS PHASE - RESEARCH ON NEW SELECTIVE CATALYSIS SYSTEMS
    HUCHETTE, D
    THERY, B
    PETIT, F
    JOURNAL OF MOLECULAR CATALYSIS, 1978, 4 (06): : 433 - 442