Organocatalytic Asymmetric Sulfa-Michael/Michael Addition Reactions: A Strategy for the Synthesis of Highly Substituted Chromans with a Quaternary Stereocenter

被引:126
作者
Wang, Xu-Fan [1 ]
Hua, Qiu-Lin [1 ]
Cheng, Ying [1 ]
An, Xiao-Lei [1 ]
Yang, Qing-Qing [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
基金
美国国家科学基金会;
关键词
heterocycles; hydrogen bonds; Michael addition; organocatalysis; synthetic methods; ENANTIOSELECTIVE TOTAL-SYNTHESIS; MICHAEL-MICHAEL CASCADE; CHIRAL BRONSTED ACIDS; VITAMIN-E; ALPHA; BETA-UNSATURATED IMIDES; BIOMIMETIC CYCLIZATION; CONJUGATE ADDITION; DOMINO REACTIONS; CONSTRUCTION; HETEROCYCLES;
D O I
10.1002/anie.201004534
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simply complex: Diverse and structurally complex chroman derivatives with a quaternary stereocenter have been obtained through the titled reaction of thiols with nitroolefin enoates using the bifunctional catalyst 1. The reaction features simple experimental procedures, high yield, enantiomeric excess, and excellent diastereoselectivity. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8379 / 8383
页数:5
相关论文
共 50 条
  • [21] Highly Efficient Catalytic Asymmetric Sulfa-Michael Addition of Thiols to trans-4,4,4-Trifluorocrotonoylpyrazole
    Dong, Xiu-Qin
    Fang, Xin
    Tao, Hai-Yan
    Zhou, Xiang
    Wang, Chun-Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1141 - 1147
  • [22] Organocatalytic Cascade Sulfa-Michael/Aldol Reaction of β,β-Disubstituted Enones: Enantioselective Synthesis of Tetrahydrothiophenes with a Trifluoromethylated Quaternary Center
    Su, Yu
    Ling, Jun-Bing
    Zhang, Shuang
    Xu, Peng-Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) : 11053 - 11058
  • [23] Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
    Tang, Cheng-Ke
    Feng, Kai-Xiang
    Xia, Ai-Bao
    Li, Chen
    Zheng, Ya-Yun
    Xu, Zhen-Yuan
    Xu, Dan-Qian
    RSC ADVANCES, 2018, 8 (06): : 3095 - 3098
  • [24] Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans
    Belmessieri, Dorine
    de la Houpliere, Alix
    Calder, Ewen D. D.
    Taylor, James E.
    Smith, Andrew D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (31) : 9762 - 9769
  • [25] Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
    Peng, Jiahuan
    Du, Da-Ming
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1210 - 1216
  • [26] NbCl5-catalyzed sulfa-Michael addition for constructing quaternary centers in enones
    Ye, Mingxia
    Xu, Yingying
    Song, Tianhang
    Gao, Zhenbo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (35) : 7100 - 7105
  • [27] Asymmetric Synthesis of Spiro β-Lactams via a Squaramide-Catalyzed Sulfa-Michael Addition/Desymmetrization Protocol
    Chauhan, Pankaj
    Mahajan, Suruchi
    Kaya, Ugur
    Valkonen, Arto
    Rissanen, Kari
    Enders, Dieter
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (20) : 3173 - 3178
  • [28] Enantioselective Sulfa-Michael Addition of Aromatic Thiols to β-Substituted Nitroalkenes Promoted by a Chiral Multifunctional Catalyst
    Wei, Qi
    Hou, Wenduan
    Liao, Na
    Peng, Yungui
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2364 - 2368
  • [29] Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst
    Saha, Prasenjit
    Biswas, Arnab
    Molleti, Nagaraju
    Singh, Vinod K.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 11115 - 11122
  • [30] Asymmetric Synthesis of Chiral Pyrrolizine-Based Triheterocycles by Organocatalytic Cascade Aza-Michael-Aldol Reactions
    Lee, Hyo-Jun
    Cho, Chang-Woo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (02) : 387 - 394