Diastereo- and enantioselective tandem Michael addition and lactonization between silyl enolates and α,β-unsaturated ketones catalyzed by a chiral quaternary ammonium phenoxide

被引：11
|
作者：
Tozawa, Takashi
Yamane, Yoshinobu
Mukaiyama, Teruaki
机构：
[1] Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
[2] Kitasato Univ, Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
来源：
CHEMISTRY LETTERS | 2006年 / 35卷 / 04期
关键词：
D O I：
10.1246/cl.2006.360
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Diastereo- and enantioselective tandem Michael addition and lactonization between various silyl enolates derived from phenyl carboxylates and alpha,beta-unsaturated ketones were successfully carried out by using an efficient organic catalyst, a cinchonidine-derived chiral quaternary ammonium phenoxide. In this asymmetric tandem reaction, the corresponding trans-3,4-dihydropyran-2-ones were obtained in high yields with almost complete diastereoselectivities and good to excellent enantioselectivities.
引用
收藏
页码：360 / 361
页数：2
相关论文
共 50 条
  • [31] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and α,β-Unsaturated Ketones
    Suo, Jia-Jia
    Du, Juan
    Liu, Qing-Rong
    Chen, Di
    Ding, Chang-Hua
    Peng, Qian
    Hou, Xue-Long
    ORGANIC LETTERS, 2017, 19 (24) : 6658 - 6661
  • [32] Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4-Conjugate Addition of β-Ketoesters to Nitroolefins
    Zhang, Hui
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (03) : 219 - 225
  • [33] High diastereo- and enantioselective Michael addition of 3-acetoxy-2-oxindoles with nitroalkenes catalyzed by nickel/PyBisulidine
    Wu, Ruoran
    Chen, Peng
    Chai, Yu
    Zhou, Junyu
    Ou, Jianhua
    Min, Yan
    Wang, Haoting
    Liang, Guojuan
    Zhang, Dong
    Zhou, Jing
    Zhou, Hui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (30) : 6225 - 6229
  • [34] Chiral Quaternary Ammonium Salt-Catalyzed Enantioselective Addition Reactions of Hydantoins
    Roeser, Katharina
    Prameshuber, Lucas
    Jahangir, Sajid
    Chandra Mallojjala, Sharath
    Hirschi, Jennifer S.
    Waser, Mario
    HELVETICA CHIMICA ACTA, 2024, 107 (03)
  • [35] Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine
    Wang, Wei
    Ye, Ling
    Shi, Zhichuan
    Zhao, Zhigang
    Li, Xuefeng
    RSC ADVANCES, 2018, 8 (73): : 41699 - 41704
  • [36] Enantioselective Michael addition of nitromethane to α,β-enones catalyzed by chiral quaternary ammonium salts.: A simple synthesis of (R)-baclofen
    Corey, EJ
    Zhang, FY
    ORGANIC LETTERS, 2000, 2 (26) : 4257 - 4259
  • [37] Enantioselective trifluoromethylation of ketones with (trifluoromethyl) trimethylsilane catalyzed by chiral quaternary ammonium phenoxides#
    Nagao, Hitoshi
    Kawano, Yoshikazu
    Mukaiyama, Teruaki
    Bulletin of the Chemical Society of Japan, 2007, 80 (12): : 2406 - 2412
  • [38] γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes
    Morrison, Ryan J.
    Hoveyda, Amir H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) : 11654 - 11661
  • [39] Diastereo- and enantioselective synthesis of carbocyclic and heterocyclic beta-amino acids by tandem aza Michael addition intramolecular cyclization
    Enders, D
    Wiedemann, J
    LIEBIGS ANNALEN-RECUEIL, 1997, (04): : 699 - 706
  • [40] Diastereo- and Enantioselective Synthesis of Functionalized Dihydropyrans via an Organocatalytic Claisen Rearrangement/Oxa-Michael Addition Tandem Sequence
    Li, Wen-Cheng
    Yang, Lei
    Wei, Zhong-Lin
    Liao, Wei-Wei
    ORGANIC LETTERS, 2023, 25 (34) : 6434 - 6439
12345