Enantioselective Assembly of Spirolactones through NHC-Catalyzed Remote γ-Carbon Addition of Enals with Isatins

被引：20
|
作者：
Rong, Xianfeng [1 ,2 ]
Yao, Hong [2 ]
Xia, Wenjing [2 ]
Du, Yonglei [1 ,2 ]
Zhou, Yu [2 ]
Liu, Hong [2 ]
机构：
[1] Univ Sci & Technol China, Nano Sci & Technol Inst, 166 Ren Ai Rd, Suzhou 215123, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
来源：
ACS COMBINATORIAL SCIENCE | 2016年 / 18卷 / 05期
基金：
中国国家自然科学基金;
关键词：
isatins; gamma-carbon; spirolactones; N-HETEROCYCLIC CARBENE; SPIROCYCLIC OXINDOLE-DIHYDROPYRANONES; COOPERATIVE CATALYSIS; CONJUGATE UMPOLUNG; SPIRO COMPOUNDS; ALPHA; BETA-UNSATURATED ALDEHYDES; QUATERNARY STEREOCENTERS; ACID; ACTIVATION; ESTERS;
D O I：
10.1021/acscombsci.5b00197
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A chiral N-heterocyclic carbene (NHC)-catalyzed formal [4+2] annulation of beta-methyl substituted enals with isatins was developed to construct six-membered spirolactones bearing highly congested quaternary carbon stereocentersin good yields and high enantioselectivities. The strategy realized a challenging remote gamma-carbon addition of enals and chiral control of beta-methyl substituted enals in the presence of the NHC catalyst only.
引用
收藏
页码：220 / 224
页数：5
相关论文
共 50 条
  • [21] Construction of alkenyl-isoquinolinones through NHC-catalyzed remote C(sp3)-H acylation and cascade cyclization of benzamides and enals
    Zeng, Rong
    Xie, Chuan
    Xing, Jin-Dun
    Dai, Hai -Yu
    He, Mei-Hao
    Xu, Peng-Shuai
    Yang, Qi-Chun
    Han, Bo
    Li, Jun-Long
    TETRAHEDRON, 2023, 132
  • [22] NHC-Catalyzed Chemoselective Reactions of Enals and Cyclopropylcarbaldehydes for Access to Chiral Dihydropyranone Derivatives
    Nong, Yingling
    Pang, Chen
    Teng, Kunpeng
    Zhang, Sheng
    Liu, Qian
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13535 - 13543
  • [23] Mechanistic study on the NHC-catalyzed [3+4] annulation of enals and thiazolones
    Li, Yan
    Li, Zhilin
    Zhang, Zhiqiang
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (27) : 12129 - 12137
  • [24] NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
    Bhunia, Anup
    Patra, Atanu
    Puranik, Vedavati G.
    Biju, Akkattu T.
    ORGANIC LETTERS, 2013, 15 (07) : 1756 - 1759
  • [25] An enantioselective assembly of naphthopyran via NHC-catalyzed [3+3] annulation of bromoenal with β-tetralone
    Li, Sha
    Yao, Yibiao
    Tang, Ziwei
    Sun, Baomin
    Yu, Chenxia
    Li, Tuanjie
    Yao, Changsheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (02) : 268 - 274
  • [26] NHC-catalyzed oxidative γ-addition of α,β-unsaturated aldehydes to isatins: a high-efficiency synthesis of spirocyclic oxindole-dihydropyranones
    Liu, Rui
    Yu, Chenxia
    Xiao, Zhaoxin
    Li, Tuanjie
    Wang, Xiangshan
    Xie, Yuanwei
    Yao, Changsheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (12) : 1885 - 1891
  • [27] Enantioselective, NHC-Catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines
    He, Ming
    Bode, Jeffrey W.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) : 418 - +
  • [28] Enantioselective, NHC-catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines
    Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106-9510, United States
    不详
    Journal of the American Chemical Society, 2008, 130 (02): : 418 - 419
  • [29] NHC-catalyzed homoenolate reaction of enals and nitroalkenes: computational study of mechanism, chemoselectivity and stereoselectivity
    Zhang, Qi
    Yu, Hai-Zhu
    Fu, Yao
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (06): : 614 - 624
  • [30] NHC-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Activation
    De Sarkar, Suman
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9266 - 9269
12345