The enantioselective construction of trifluoromethylated quaternary stereocenters via the Rh-catalyzed asymmetric dehydrated arylation of unprotected hemiaminals

被引:7
作者
Sun, Yu-Tuo [1 ,2 ]
Zhu, Dong-Xing [1 ,2 ]
Rao, Xiaofeng [3 ,4 ]
Xu, Ming-Hua [1 ,2 ,3 ,4 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chongzhi Rd, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Sch Pharm, 555 Zu Chongzhi Rd, Shanghai 201203, Peoples R China
[3] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Blvd, Shenzhen 518055, Peoples R China
[4] Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Blvd, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
CHIRAL DIENE LIGANDS; OLEFIN LIGANDS; ORGANOBORON REAGENTS; KETIMINES SYNTHESIS; ARYLBORONIC ACIDS; PHOSPHITE-OLEFIN; SULFUR-OLEFINS; ACCESS; EFFICIENT; ACTIVATION;
D O I
10.1039/c9qo01203f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the highly enantioselective Rh-catalyzed dehydrated arylation of unprotected hemiaminals has been developed, and provided a series of chiral benzosultams bearing trifluoromethylated quaternary stereocenters in high yields with excellent enantioselectivities (up to 99% ee). The synthetic utility was further demonstrated by the facile enantioselective construction of a HIV-1 inhibitor molecule.
引用
收藏
页码:340 / 344
页数:5
相关论文
共 65 条
  • [1] Dehydrative Mannich-Type Reaction for the Synthesis of Azepinobisindole Alkaloid Iheyamine A
    Abe, Takumi
    Yamada, Koji
    [J]. ORGANIC LETTERS, 2018, 20 (05) : 1469 - 1472
  • [2] BAKER DC, 2003, Patent No. 6562850
  • [3] BAKER DC, 2000, Patent No. 0004004
  • [4] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [5] Organic fluorine compounds: a great opportunity for enhanced materials properties
    Berger, Ricarda
    Resnati, Giuseppe
    Metrangolo, Pierangelo
    Weber, Edwin
    Hulliger, Juerg
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3496 - 3508
  • [6] Billard T, 2001, EUR J ORG CHEM, V2001, P1467
  • [7] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
    Charpentier, Julie
    Frueh, Natalja
    Togni, Antonio
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682
  • [8] Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to lmines
    Chen, Diao
    Xu, Ming-Hua
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1589 - 1612
  • [9] Rhodium(I)-Catalyzed Asymmetric Carbene Insertion into B-H Bonds: Highly Enantioselective Access to Functionalized Organoboranes
    Chen, Diao
    Zhang, Xu
    Qi, Wei-Yi
    Xu, Bin
    Xu, Ming-Hua
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (16) : 5268 - 5271
  • [10] Enantioselective Rhodium-Catalyzed Arylation of Cyclic N-Sulfamidate Alkylketimines: A New Access to Chiral β-Alkyl-β-aryl Amino Alcohols
    Chen, Ya-Jing
    Chen, Ya-Heng
    Feng, Chen-Guo
    Lin, Guo-Qiang
    [J]. ORGANIC LETTERS, 2014, 16 (12) : 3400 - 3403