Synthesis of Spiranes by Thiol-Mediated Acyl Radical Cyclization

被引:20
|
作者
Hsu, Day-Shin [1 ]
Chen, Chih-Hao [1 ]
Hsu, Chi-Wei [1 ]
机构
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Minhsiung 621, Taiwan
关键词
Synthetic methods; Cyclization; Radical reactions; Spiro compounds; Acyl radicals; Acylation; CARBOCYCLIC SPIRO COMPOUNDS; OXIDATION;
D O I
10.1002/ejoc.201501305
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and efficient method for the preparation of spiro compounds is described. Various enone-aldehydes were exposed to t-dodecanethiol and AIBN at 75 degrees C in toluene to afford spirocyclic 1,4-diketones in moderate to good yields.
引用
收藏
页码:589 / 598
页数:10
相关论文
共 50 条
  • [1] Stereoselective Formal Synthesis of (+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization
    Yamada, Ken-ichi
    Sato, Tomohiro
    Hosoi, Masaki
    Yamamoto, Yasutomo
    Tomioka, Kiyoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) : 1511 - 1516
  • [2] THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES
    BACHI, MD
    BALANOV, A
    BARNER, N
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25): : 7752 - 7758
  • [3] Thiol-mediated radical cyclizations
    Majumdar, Krishna C.
    Debnath, Pradip
    TETRAHEDRON, 2008, 64 (42) : 9799 - 9820
  • [4] Thiol-mediated radical cyclization: regioselective formation of indole-annulated sulfur heterocycles by tandem cyclization
    Majumdar, K. C.
    Debnath, P.
    Alam, S.
    Maji, P. K.
    TETRAHEDRON LETTERS, 2007, 48 (39) : 7031 - 7033
  • [5] Thiol-catalyzed acyl radical cyclization of alkenals
    Yoshikai, K
    Hayama, T
    Nishimura, K
    Yamada, K
    Tomioka, K
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02): : 681 - 683
  • [6] Thiol-mediated free radical formation from oxidized protein
    Morimitsu, Y
    Shimada, M
    Osawa, T
    Uchida, K
    FREE RADICAL BIOLOGY AND MEDICINE, 1998, 25 : S76 - S76
  • [7] Thiol-Mediated Uptake
    Laurent, Quentin
    Martinent, Remi
    Lim, Bumhee
    Anh-Tuan Pham
    Kato, Takehiro
    Lopez-Andarias, Javier
    Sakai, Naomi
    Matile, Stefan
    JACS AU, 2021, 1 (06): : 710 - 728
  • [8] Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization
    McCourt, Ruairi O.
    Denes, Fabrice
    Sanchez-Sanz, Goar
    Scanlan, Eoin M.
    ORGANIC LETTERS, 2018, 20 (10) : 2948 - 2951
  • [9] Thiol-mediated free radical cyclisations of isocyanides on solid support
    Lamberto, M
    Corbett, DF
    Kilburn, JD
    TETRAHEDRON LETTERS, 2004, 45 (46) : 8541 - 8543
  • [10] Inhibitors of thiol-mediated uptake
    Cheng, Yangyang
    Pham, Anh-Tuan
    Kato, Takehiro
    Lim, Bumhee
    Moreau, Dimitri
    Lopez-Andarias, Javier
    Zong, Lili
    Sakai, Naomi
    Matile, Stefan
    CHEMICAL SCIENCE, 2021, 12 (02) : 626 - 631