An efficient oxa-Michael addition to diethyl vinylphosphonate under mild reaction conditions

被引:12
|
作者
Baszczynski, Ondrej [1 ]
Jansa, Petr [1 ]
Dracinsky, Martin [1 ]
Kaiser, Martin Maxmilian [1 ]
Spacek, Petr [1 ]
Janeba, Zlatko [1 ]
机构
[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Vvi, CR-16610 Prague 6, Czech Republic
来源
RSC ADVANCES | 2012年 / 2卷 / 04期
关键词
ACYCLIC NUCLEOSIDE PHOSPHONATES; HYPOXANTHINE-GUANINE PHOSPHORIBOSYLTRANSFERASE; DERIVATIVES; INHIBITION; RESISTANCE; ANALOGS; TARGET; WATER; ACIDS; DNA;
D O I
10.1039/c2ra00938b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An oxa-Michael addition of various secondary and branched primary alcohols to diethyl vinylphosphonate was systematically studied and optimized. This efficient method precedes using of harsh reaction conditions (e.g. strong bases, high temperatures) and gains access to an important class of biologically active compounds in one step.
引用
收藏
页码:1282 / 1284
页数:3
相关论文
共 50 条
  • [41] An Efficient Ecofriendly Enantioselective Organocatalytic Ring-Closing Reaction of 2-Hydroxychalcone via Intramolecular Oxa-Michael Reaction
    Singh, Ashawani Kumar
    Mangawa, Shrawan Kumar
    Kumar, Arvind
    Dixit, A. K.
    Awasthi, Satish Kumar
    CHEMISTRYSELECT, 2017, 2 (34): : 11160 - 11163
  • [42] The oxa-Michael reaction:: from recent developments to applications in natural product synthesis
    Nising, Carl F.
    Braese, Stefan
    CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) : 1218 - 1228
  • [43] Concise Synthesis of Tetrahydropyrans by a Tandem Oxa-Michael/Tsuji-Trost Reaction
    Wang, Liang
    Li, Pengfei
    Menche, Dirk
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9270 - 9273
  • [44] Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes
    Parhi, Biswajit
    Gurjar, Jitendra
    Pramanik, Suman
    Midya, Abhisek
    Ghorai, Prasanta
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4654 - 4663
  • [45] A One-Pot Deprotection and Intramolecular Oxa-Michael Addition to Access Angular Trioxatriquinanes
    Ramakrishna, Kota
    Kaliappan, Krishna P.
    SYNLETT, 2011, (17) : 2580 - 2584
  • [46] Organocatalytic Asymmetric Dearomative Spirocyclization/Oxa-Michael Addition Sequence: Synthesis of Polycyclic Tetralones
    Meher, Ramji
    Pan, Subhas Chandra
    ORGANIC LETTERS, 2024, 26 (15) : 3179 - 3183
  • [47] Stereoselective Oxa-Michael Addition of Tyrosine to Propargyl Aldehyde/Esters: Formation of Benzofurans and Flavones
    Vasconcelos, Stanley N. S.
    de Oliveira, Isadora Maria
    Shamim, Anwar
    Zukerman-Schpector, Julio
    Pimenta, Daniel C.
    Stefani, Helio A.
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4243 - 4254
  • [48] Organocatalytic enantioselective synthesis of phthalans via Wittig/oxa-Michael cascade reaction
    Son, Eun Chae
    No, Jaeeun
    Kim, Sung-Gon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (11) : 1473 - 1480
  • [49] Structural Diversification of Pyrazinone Metabolites via Spontaneous Oxa-Michael Addition in Staphylococcus xylosus
    Lee, Ju Ryeong
    Hwang, Su Jung
    Choi, Yukyung
    Kim, Jonghwan
    Lee, Gyu Sung
    Lee, Bum Soo
    Kim, Ki Hyun
    Kang, Kyo Bin
    Lee, Hyo-Jong
    Kim, Chung Sub
    JOURNAL OF NATURAL PRODUCTS, 2024, 87 (07): : 1881 - 1887
  • [50] Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction
    Xiong, Fangjun
    Wang, Haifeng
    Yan, Lingjie
    Xu, Lingjun
    Tao, Yuan
    Wu, Yan
    Chen, Fener
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (38) : 9813 - 9819