Facile Synthesis of δ-Amino-β-ketoesters and Piperidinediones via a Vinylogous Mannich-Type Reaction of Brassard-Type Diene with Aldimines without Catalyst

被引：5
|
作者：
Gu, Chun-Ling [1 ]
Liu, Li [1 ]
Wang, Dong [1 ]
Chen, Yong-Jun [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, BNLMS, Biol Chem Lab, Beijing 100080, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 16期
基金：
中国国家自然科学基金;
关键词：
Catalyst-free; one-pot process; piperidinedione; vinylogous Mannich; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; FORMAL SYNTHESIS; ALKALOIDS; CYCLOADDITION; GLUTARIMIDES; INHIBITOR; ACID;
D O I：
10.1080/00397910902730846
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The vinylogous Mannich reaction of N-tosyl-aldimines with Brassard diene proceeds at room temperature under catalyst-free conditions smoothly to give gamma-amino-beta-ketoesters (4b-l) in good to excellent yields, which are easily converted to piperidinediones at higher temperature. The two-step reactions could be combined in a one-pot process with toluene as a solvent and without the use of any catalyst for direct synthesis of piperidinediones (5).
引用
收藏
页码：2989 / 3002
页数：14
相关论文
共 50 条
  • [1] Stereoselective synthesis of δ-amino-α,β,γ,δ-unsaturated cycloketones via Mannich-type reaction
    He, Long
    Qin, Xue
    Qin, Xiao-Yan
    He, Chun-Lan
    Wang, Shi-Da
    Hao, Wen-Juan
    Jiang, Bo
    TETRAHEDRON LETTERS, 2020, 61 (17)
  • [2] Mannich-type reaction with trifluoromethylated N,O-hemiacetal:: Facile preparation of β-amino-β-trifluoromethyl carbonyl compounds
    Takaya, J
    Kagoshima, H
    Akiyama, T
    ORGANIC LETTERS, 2000, 2 (11) : 1577 - 1579
  • [3] Facile and diastereoselective synthesis of β-acetamido ketones and keto esters via direct Mannich-type reaction
    Mao, Hui
    Wan, Jieping
    Pan, Yuanjiang
    TETRAHEDRON, 2009, 65 (05) : 1026 - 1032
  • [4] Catalyst-free Synthesis of Betti bases in a Mannich-Type Reaction
    Kidwai, Mazaahir
    Chauhan, Ritika
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (05) : 395 - 398
  • [5] An efficient synthesis of β-amino esters via Zn(OTf)2-catalyzed Mannich-type reaction
    Shou, WG
    Yang, YY
    Wang, YG
    TETRAHEDRON LETTERS, 2006, 47 (11) : 1845 - 1847
  • [6] Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid
    Wu, Hui
    Shen, Yang
    Fan, Li-yan
    Wan, Yu
    Zhang, Pu
    Chen, Cai-fa
    Wang, Wen-xiang
    TETRAHEDRON, 2007, 63 (11) : 2404 - 2408
  • [7] Organocatalytic enantioselective Mannich-type reaction of phosphorus ylides:: Synthesis of chiral N-Boc-β-amino-α-methylene carboxylic esters
    Zhang, Yan
    Liu, Yan-Kai
    Kang, Tai-Ran
    Hu, Ze-Kai
    Chen, Ying-Chun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) : 2456 - 2457
  • [8] New Synthesis of Trifluoromethyl Aldimines Containing L--Amino Ester Moieties and Their Use in Mannich-Type Reactions
    Parise, Luca
    Pelagalli, Alessia
    Trulli, Laura
    Vergari, Maria Cecilia
    Fioravanti, Stefania
    Pellacani, Lucio
    CHIRALITY, 2015, 27 (09) : 571 - 575
  • [9] Organocatalytic enantioselective Mannich-type reaction of phosphorus ylides: Synthesis of chiral N-Boc-β-amino-α-methylene carboxylic esters
    Zhang, Yan
    Liu, Yan-Kai
    Kang, Tai-Ran
    Hu, Ze-Kai
    Chen, Ying-Chun
    Journal of the American Chemical Society, 2008, 130 (08): : 2456 - 2457
  • [10] Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines
    Zheng, Jianfeng
    Lin, Lili
    Fu, Kai
    Zheng, Haifeng
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8836 - 8842
12345