Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of γ-difluoromethylated γ-lactams

被引：28
|
作者：
Pharikronburee, Vannapha
Punirun, Teerachai
Soorukram, Darunee
Kuhakarn, Chutima
Tuchinda, Patoomratana
Reutrakul, Vichai
Pohmakotr, Manat [1 ]
机构：
[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 12期
关键词：
OXIDATIVE TRIFLUOROMETHYLATION; ELECTROPHILIC FLUORINATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC FLUORINATION; ARYL; CYCLIZATION; STRATEGY; ACIDS; ME3SICF2SPH; SULFOXIDES;
D O I：
10.1039/c3ob27193e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
PhSCF2SiMe3 (1) underwent fluoride-catalyzed nucleophilic addition to the carbonyl group of anhydrides to provide the corresponding gamma-difluoro(phenylsulfanyl) methyl gamma-lactols, which were employed for the synthesis of gamma-difluoromethylated gamma-lactams.
引用
收藏
页码：2022 / 2033
页数：12
相关论文
共 50 条
  • [1] Fluoride-Catalyzed Nucleophilic Addition of PhSCF2SiMe3 to Isatins: Synthesis of 3-(1,1-Difluoroalkyl)-3-hydroxyindolin-2-ones
    Keereewan, Sirisuk
    Soorukram, Darunee
    Kuhakarn, Chutima
    Reutrakul, Vichai
    Pohmakotr, Manat
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) : 295 - 305
  • [2] Stereoselective Nucleophilic Addition of PhSCF2SiMe3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem-Difluoromethylenated Polyhydroxypyrrolizidines and -indolizidines
    Korvorapun, Korkit
    Soorukram, Darunee
    Kuhakarn, Chutima
    Tuchinda, Patoomratana
    Reutrakul, Vichai
    Pohmakotr, Manat
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (04) : 948 - 968
  • [3] Fluoride-Catalyzed Addition of PhSCF2SiMe3 to N-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of gem-Difluoromethylenated 1-Azabicyclic Compounds
    Bootwicha, Teerawut
    Panichakul, Duanghathai
    Kuhakarn, Chutima
    Prabpai, Samran
    Kongsaeree, Palangpon
    Tuchinda, Patoomratana
    Reutrakul, Vichai
    Pohmakotr, Manat
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3798 - 3805
  • [4] Synthesis of γ-Difluoromethyl α,β-Unsaturated γ-Butyrolactones Using PhSCF2SiMe3 as a Difluoromethylating Agent
    Issaree, Arisara
    Masusai, Chonticha
    Soorukram, Darunee
    Kuhakarn, Chutima
    Reutrakul, Vichai
    Pohmakotr, Manat
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (17) : 3751 - 3759
  • [5] Application of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Fluoride-Catalyzed Addition to N-Substituted Cyclic Imides Followed by Radical Cyclization
    Chernykh, Yana
    Opekar, Stanislav
    Klepetarova, Blanka
    Beier, Petr
    SYNLETT, 2012, (08) : 1187 - 1190
  • [6] Synthesis of gem-Difluoromethylenated Compounds Employing α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a gem-Difluoromethylene Building Block
    Soorukram, Darunee
    Kuhakarn, Chutima
    Reutrakul, Vichai
    Pohmakotr, Manat
    SYNLETT, 2014, 25 (18) : 2558 - 2573
  • [7] FLUORIDE-CATALYZED MICHAEL-ADDITION OF 2,2,2-TRIFLUORONITROALKANES TO ACTIVATED MONDOLEFINS
    BAASNER, B
    MARHOLD, A
    NEGELE, M
    JOURNAL OF FLUORINE CHEMISTRY, 1990, 46 (01) : 161 - 172
  • [8] SYNTHESIS OF 1,4-DIKETONES BY FLUORIDE-CATALYZED MICHAEL ADDITION AND SUPPORTED PERMANGANATE OXIDATION
    CLARK, JH
    CORK, DG
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) : 635 - 636
  • [9] Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert- Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles
    Keereewan, Sirisuk
    Kuhakarn, Chutima
    Leowanawat, Pawaret
    Saithong, Saowanit
    Reutrakul, Vichai
    Soorukram, Darunee
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (23): : 15963 - 15985
  • [10] THE SYNTHESIS OF 1,4-DIKETONES VIA FLUORIDE-CATALYZED MICHAEL ADDITION AND SUPPORTED-PERMANGANATE-PROMOTED NEF TRANSFORMATION
    CLARK, JH
    CORK, DG
    GIBBS, HW
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (09): : 2253 - 2258
12345