Modified Julia-Kocienski Reaction Promoted by Means of m-NPT (Nitrophenyltetrazole) Sulfone

被引:10
|
作者
Sakai, Yuki
Ikeuchi, Kazutada
Yamada, Yuji
Wakimoto, Toshiyuki
Kan, Toshiyuki [1 ]
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
关键词
olefination; Julia-Kocienski reaction; sulfone; STEREOSELECTIVE-SYNTHESIS; CONDENSATION; ALDEHYDES;
D O I
10.1055/s-0029-1219386
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
m-Nitrophenyltetrazole sulfone (2) was employed in the Julia-Kocienski reaction. The olefination reaction between 2 and carbonyl compounds proceeded smoothly under Masamune-Roush conditions (DBU and LiCl). These conditions were also applicable to our catechin derivative synthesis. Furthermore, phenolic mesylate was also tolerated in this mild reaction.
引用
收藏
页码:827 / 829
页数:3
相关论文
共 23 条
  • [21] Synthesis of Iriomoteolide-1a C13-C23 Fragment via Asymmetric Conjugate Addition and Julia-Kocienski Coupling Reaction
    Chin, Yen-Jin
    Wang, Shun-Yi
    Loh, Teck-Peng
    ORGANIC LETTERS, 2009, 11 (16) : 3674 - 3676
  • [22] The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia-Kocienski reaction
    Rehman, Mintu
    Surendran, Sravya
    Siddavatam, Nagendra
    Rajendar, Goreti
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (02) : 329 - 333
  • [23] 1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia-Kocienski olefination
    Zhu, Lingui
    Ni, Chuanfa
    Zhao, Yanchuan
    Hu, Jinbo
    TETRAHEDRON, 2010, 66 (27-28) : 5089 - 5100