Allylic alcohols as radical allylating agents. An overall olefination of aldehydes and ketones

被引:37
|
作者
Charrier, Nicolas [1 ]
Quiclet-Sire, Beatrice [1 ]
Zard, Samir Z. [1 ]
机构
[1] Ecole Polytech, CNRS, Synth Organ Lab, UMR 7652, F-91128 Palaiseau, France
关键词
D O I
10.1021/ja802899m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Fluoroyridynl derivatives of allylic alcohols react with xanthates in the presence of lauroyl peroxide to give alkenes, often with high stereoselectivity. If the allylic alcohols are themselves derived from aldehydes or ketones, the overall process becomes a synthetic equivalent of the classical Witting and related olefination reactions.
引用
收藏
页码:8898 / +
页数:3
相关论文
共 50 条
  • [31] Metal-Free Oxidative Radical Addition of Carbonyl Compounds to α,α-Diaryl Allylic Alcohols: Synthesis of Highly Functionalized Ketones
    Chu, Xue-Qiang
    Meng, Hua
    Zi, You
    Xu, Xiao-Ping
    Ji, Shun-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) : 17198 - 17206
  • [32] Aerobic Oxidative Coupling between Carbon Nucleophiles and Allylic Alcohols: A Strategy to Construct β-(Hetero)Aryl Ketones and Aldehydes through Hydrogen Migration
    Huang, Liangbin
    Qi, Ji
    Wu, Xia
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (46) : 15462 - 15466
  • [33] PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .2. SYNTHESIS OF ARYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ARYL HALIDES AND UNSATURATED ALCOHOLS
    CHALK, AJ
    MAGENNIS, SA
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07): : 1206 - 1209
  • [34] Characterization of an Allylic/Benzyl Alcohol Dehydrogenase from Yokenella sp Strain WZY002, an Organism Potentially Useful for the Synthesis of α,β-Unsaturated Alcohols from Allylic Aldehydes and Ketones
    Ying, Xiangxian
    Wang, Yifang
    Xiong, Bin
    Wu, Tingting
    Xie, Liping
    Yu, Meilan
    Wang, Zhao
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2014, 80 (08) : 2399 - 2409
  • [35] SYNTHESIS OF ARYL-SUBSTITUTED ALDEHYDES AND KETONES VIA PALLADIUM-CATALYZED COUPLING OF ARYL HALIDES AND NON-ALLYLIC UNSATURATED ALCOHOLS
    LAROCK, RC
    LEUNG, WY
    STOLZDUNN, S
    TETRAHEDRON LETTERS, 1989, 30 (48) : 6629 - 6632
  • [36] Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of β-Aryl Ketones and Aldehydes
    Liao, Jianhua
    Zhang, Zhenming
    Tang, Xiaodong
    Wu, Wanqing
    Guo, Wei
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8903 - 8909
  • [37] Selective Synthesis of Ketones and Chiral Allylic Alcohols from the Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Mediated by a Transition Metal/Monophosphorus Ligand System
    Miao, Rui
    Huang, Jinyong
    Xia, Yanping
    Wei, YiFei
    Luo, Renshi
    Ouyang, Lu
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8576 - 8588
  • [38] SILICA-GEL SUPPORTED ZINC BOROHYDRIDE .2. REGIOSELECTIVE 1,2-REDUCTION OF CONJUGATED KETONES AND ALDEHYDES TO THE CORRESPONDING ALLYLIC ALCOHOLS
    RANU, BC
    DAS, AR
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15): : 4796 - 4798
  • [39] Recyclable Au0, Ag0 and Au0-Ag0 nanocolloids for the chemoselective hydrogenation of α,β-unsaturated aldehydes and ketones to allylic alcohols
    Mertens, Pascal G. N.
    Vandezande, Pieter
    Ye, Xingpu
    Poelman, Hilde
    Vankelecom, Ivo F. J.
    De Vos, Dirk E.
    APPLIED CATALYSIS A-GENERAL, 2009, 355 (1-2) : 176 - 183
  • [40] Radical cyclization in heterocycle synthesis. 6. A new entry to cyclic amino alcohols via stannyl radical cyclization of oxime ethers connected with aldehydes or ketones
    Naito, T
    Nakagawa, K
    Nakamura, T
    Kasei, A
    Ninomiya, I
    Kiguchi, T
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06): : 2003 - 2009