Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine

被引:0
|
作者
Wei, Xiao-Hong [1 ]
Xue, Ya-Wen [1 ]
Liu, Xuan [1 ]
Wang, Xiao-Hong [1 ]
Wang, Yan-Bin [1 ]
Su, Qiong [1 ]
机构
[1] Northwest Minzu Univ, Coll Chem Engn, Key Lab Environm Friendly Composite Mat, Key Lab Util Environm Friendly Composite Mat & Bio, Lanzhou 730030, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期
基金
中国国家自然科学基金;
关键词
MORITA-BAYLIS-HILLMAN; 4+1 ANNULATION; C BOND; CARBONATES; OXIDES; CONSTRUCTION; ALLENES; ACCESS; ACID; 3-NITROINDOLES;
D O I
10.1021/acs.joc.4c01860
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for phosphine-catalyzed sulfophosphinoylation of alpha,beta-unsaturated ketones for synthesis allylic organophosphorus compounds has been reported, in which alpha,beta-unsaturated compounds acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond and a C-O bond and obtain allylic organophosphorus with high regio- and stereoselectivity in moderate to excellent yields.
引用
收藏
页码:16564 / 16570
页数:7
相关论文
共 50 条
  • [1] KF-Montmorillonite-catalyzed Michael Addition Reaction of Malononitrile to α,β-Unsaturated Ketones
    Shi Daqing
    Wu Nan
    Zhuang Qiya
    CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (01) : 169 - 173
  • [2] Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones
    Lu, Min
    Li, Hong
    Zou, Chuncheng
    Li, Jianchang
    Liu, Chengyu
    Sun, Maolin
    Ma, Yueyue
    Cheng, Ruihua
    Ye, Jinxing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (42) : 9305 - 9312
  • [3] Direct Asymmetric Michael Reaction of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Two Secondary Amine Catalysts
    Hayashi, Yujiro
    Umekubo, Nariyoshi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) : 1958 - 1962
  • [4] Michael Addition Reaction of Malononitrile and α,β-Unsaturated Ketones Catalyzed by Amine Functionalized MCM-41
    Wang, Changchun
    Xie, Shaolei
    Xie, Zhengfeng
    Hui, Yonghai
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (11) : 2391 - 2395
  • [5] Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional N-Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent
    Huang, Hai
    Kang, Jun Yong
    ORGANIC LETTERS, 2016, 18 (17) : 4372 - 4375
  • [6] SELECTIVE REDUCTION OF UNSATURATED-KETONES TO UNSATURATED ALCOHOLS CATALYZED BY AN IRIDIUM PHOSPHINE SYSTEM
    VISINTIN, M
    SPOGLIARICH, R
    KASPAR, J
    GRAZIANI, M
    JOURNAL OF MOLECULAR CATALYSIS, 1984, 24 (03): : 277 - 280
  • [7] Organocatalytic Domino Michael-Aldol Reaction of Ketones and α,β-Unsaturated Trifluoromethyl Ketones
    Wang, Xiao-Jin
    Zhao, Yan
    Liu, Jin-Tao
    SYNTHESIS-STUTTGART, 2008, Georg Thieme Verlag (24): : 3967 - 3973
  • [8] Enantioselective organocatalytic phospha-Michael reaction of α,β-unsaturated ketones
    Wen, Shigang
    Li, Pengfei
    Wu, Haibo
    Yu, Feng
    Liang, Xinmiao
    Ye, Jinxing
    CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4806 - 4808
  • [9] The Michael addition of indole to α,β-unsaturated ketones catalyzed by iodine at room temperature
    Wang, SY
    Ji, SJ
    Loh, TP
    SYNLETT, 2003, (15) : 2377 - 2379
  • [10] Antimony trichloride-catalyzed Michael addition of indoles to the α,β-unsaturated ketones
    Maiti, Gourhari
    Kundu, Pradip
    SYNTHETIC COMMUNICATIONS, 2007, 37 (14) : 2309 - 2316