Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins

被引：247
|
作者：
Wang, J [1 ]
Li, H
Duan, WH
Zu, LS
Wang, W
机构：
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
[2] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 21期
关键词：
D O I：
10.1021/ol0519137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel binaphthyl-derived amine thiourea organocatalyst has been developed and demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol % loading) of diketones to nitroalkenes with remarkably high enantioselectivities.
引用
收藏
页码：4713 / 4716
页数：4
相关论文
共 50 条
  • [21] KNOEVENAGEL CONDENSATIONS WITH TICL4 BASE .5. 3-ALKYLIDENE-2,4-PENTANDIONE AND 3-ARYLIDENE-2,4-PENTANDIONE FROM ALDEHYDES AND ACETYL ACETONE
    LEHNERT, W
    SYNTHESIS-STUTTGART, 1974, (09): : 667 - 669
  • [22] Enantioselective organocatalytic Michael addition reactions between N-heterocycles and nitroolefins
    Wang, J
    Li, H
    Zu, LS
    Wang, W
    ORGANIC LETTERS, 2006, 8 (07) : 1391 - 1394
  • [23] ORGN 147-Organocatalytic enantioselective Michael addition of thioacetic to nitroolefins and enones
    Li, Hao
    Wang, Jian
    Zu, Liansuo
    Wang, Wei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [24] Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins
    Preegel, Gert
    Noole, Artur
    Ilmarinen, Kaja
    Jaerving, Ivar
    Kanger, Tonis
    Pehk, Tonis
    Lopp, Margus
    SYNTHESIS-STUTTGART, 2014, 46 (19): : 2595 - 2600
  • [25] Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent Quaternary and Tertiary Stereocenters
    Jin, Cheng-Yong
    Wang, Yao
    Liu, Yao-Zong
    Shen, Chao
    Xu, Peng-Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24): : 11307 - 11312
  • [26] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
    Andrey, O
    Alexakis, A
    Bernardinelli, G
    ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
  • [27] Organocatalytic Asymmetric Michael Addition/Carbon-Carbon Bond Cleavage of Trifluoromethyl α-Fluorinated gem-Diols to Nitroolefins
    Saidalimu, Ibrayim
    Fang, Xiang
    Lv, Wenwen
    Yang, Xueyan
    He, Xiaopeng
    Zhang, Jingyuan
    Wu, Fanhong
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 857 - 863
  • [28] Asymmetric organocatalytic Michael addition of ketones to vinyl sulfone
    Zhu, Qiang
    Cheng, Lili
    Lu, Yixin
    CHEMICAL COMMUNICATIONS, 2008, (47) : 6315 - 6317
  • [29] Organocatalytic Asymmetric Michael Addition of α-Fluoro β-Ketophosphonate to Nitroalkenes
    Jeong, Hyun Jung
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (12) : 2936 - 2939
  • [30] Regioselective and diastereodivergent organocatalytic asymmetric vinylogous Michael addition
    Zou, Chuncheng
    Lv, Yanting
    Lu, Min
    Li, Xin
    Zhang, Lei
    Yang, Lei
    Liu, Zhen
    Ke, Yanxiong
    Song, Gonghua
    Ye, Jinxing
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (17) : 4758 - 4766
12345