An unexpected tandem enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β,γ-unsaturated α-keto esters catalyzed by cinchona alkaloids

被引：18
|
作者：
Wang, Hai-Feng [1 ]
Zheng, Chang-Wu [1 ]
Yang, Ying-Quan [2 ]
Chai, Zhuo [1 ]
Zhao, Gang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 22期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/j.tetasy.2008.11.007
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Cinchona alkaloids were found to catalyze an enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of beta,gamma-unsaturated alpha-keto esters 1 and malonates 2. Using the optimum catalyst quinine 4a, a series of the rearranged products 3 were obtained with up to 98% yield and 82% ee under mild reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2608 / 2615
页数：8
相关论文
共 50 条
  • [41] Bifunctional Cinchona Alkaloid Catalyzed Vinylogous Michael Reaction of 3-Alkylideneoxindole with 4-Oxo-enoates: A Route to Chiral γ-Keto Alkylideneoxindole Esters
    Kumar, Rajesh
    Jaiswal, Manish K.
    Singh, Ravi P.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1576 - 1580
  • [42] TANDEM 1,4-DIAZA,3-OXA-COPE REARRANGEMENT NUCLEOPHILIC-ADDITION REACTION - A ROUTE TO 2-OXOBENZIMIDAZOLES
    SACZEWSKI, F
    DEBOWSKI, T
    TETRAHEDRON LETTERS, 1993, 34 (17) : 2843 - 2846
  • [43] Copper-Catalyzed Enantioselective Mukaiyama Aldol Reaction of Silyl Enol Ethers with Isatin-Derived Oxindolyl β,γ-Unsaturated α-Keto Esters
    Lu, Wenjing
    Li, Jindong
    Lu, Yangmian
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRYSELECT, 2021, 6 (03): : 410 - 414
  • [44] Enantioselective Synthesis of Highly Substituted Chromans by a Zinc(II)-Catalyzed Tandem Friedel-Crafts Alkylation/Michael Addition Reaction
    Li, Chao
    Liu, Feng-Lei
    Zou, You-Quan
    Lu, Liang-Qiu
    Chen, Jia-Rong
    Xiao, Wen-Jing
    SYNTHESIS-STUTTGART, 2013, 45 (05): : 601 - 608
  • [45] Michael addition of stannyl ketone enolate to α,β-unsaturated esters catalyzed by tetrabutylammonium bromide and an ab initio theoretical study of the reaction course
    Yasuda, Makoto
    Chiba, Kouji
    Ohigashi, Noriyuki
    Katoh, Yasuhiro
    Baba, Akio
    Baba, A. (baba@chem.eng.osaka-u.ac.jp), 1600, American Chemical Society (125):
  • [46] Michael addition of stannyl ketone enolate to α,β-unsaturated esters catalyzed by tetrabutylammoniurn bromide and an ab initio theoretical study of the reaction course
    Yasuda, M
    Chiba, K
    Ohigashi, N
    Katoh, Y
    Baba, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (24) : 7291 - 7300
  • [47] Enantioselective 1,4-Michael addition reaction of pyrazolin-5-one derivatives with 2-enoylpyridines catalyzed by Cinchona derived squaramides
    Sharma, Vivek
    Kaur, Anmolpreet
    Sahoo, Subash Chandra
    Chimni, Swapandeep Singh
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (35) : 6470 - 6478
  • [48] Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α, β-unsaturated ketones
    Goyal, Pooja
    Dubey, Akhil K.
    Chowdhury, Raghunath
    Wadawale, Amey
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1518 - 1526
  • [49] Synthesis of β,β-Disubstituted lndanones via the Pd-Catalyzed Tandem Conjugate Addition/Cyclization Reaction of Arylboronic Acids with α,β-Unsaturated Esters
    Gao, Ang
    Liu, Xiu-Yan
    Li, Hao
    Ding, Chang-Hua
    Hou, Xue-Long
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 9988 - 9994
  • [50] Highly Enantioselective Michael Addition of α-Substituted Cyano Ketones to β,γ-Unsaturated α-Keto Esters using Bifunctional Thiourea-Tertiary Amine Catalysts: An Easy Access to Chiral Dihydropyrans
    Zhao, Sheng-Li
    Zheng, Chang-Wu
    Wang, Hai-Feng
    Zhao, Gang
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2811 - 2816
12345