Iridium-Catalyzed Enantioselective Allylic Substitution of O-Allyl Carbamothioates

被引:29
|
作者
Xu, Qing-Long [1 ]
Liu, Wen-Bo [1 ]
Dai, Li-Xin [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 13期
基金
中国国家自然科学基金;
关键词
S BOND FORMATION; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; AMINATION; ETHERIFICATION; COMPLEXES; ALCOHOLS; THIOLS; HETEROCYCLES; ALKYLATION;
D O I
10.1021/jo1006152
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
With an [Ir(COD)Cl](2)/phosphoramidite ligand system, an allylic substitution of O-allyl carbamothioates was developed. The reaction proceeded in the favor of branched products with up to 93:7 branched-to-linear ratio, affording chiral S-allyl carbamothioates with up to 95% ee.
引用
收藏
页码:4615 / 4618
页数:4
相关论文
共 50 条
  • [21] Enantioselective synthesis of 10-allylanthrones via iridium-catalyzed allylic substitution reaction
    Zheng-Le Zhao
    Qing Gu
    Xin-Yan Wu
    Shu-Li You
    ChineseChemicalLetters, 2016, 27 (05) : 619 - 622
  • [22] Iridium-Catalyzed Enantioselective Allylic Substitution of Unstabilized Enolates Derived from α,β-Unsaturated Ketone
    Chen, Ming
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8691 - 8695
  • [23] Enantioselective synthesis of 10-allylanthrones via iridium-catalyzed allylic substitution reaction
    Zhao, Zheng-Le
    Gu, Qing
    Wu, Xin-Yan
    You, Shu-Li
    CHINESE CHEMICAL LETTERS, 2016, 27 (05) : 619 - 622
  • [24] Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides
    Chen, Ming
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13972 - 13979
  • [25] Iridium-catalyzed enantioselective allyl-alkene coupling
    Carreira, E.M. (carreira@org.chem.ethz.ch), 1600, American Chemical Society (136):
  • [26] Iridium-Catalyzed Enantioselective Allyl-Alkene Coupling
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (08) : 3006 - 3009
  • [27] Iridium-Catalyzed Enantioselective Allylic Vinylation with Potassium Alkenyltrifluoroborates
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    Liu, Wen-Bo
    Han, Seo-Jung
    Stoltz, Brian M.
    ORGANIC SYNTHESES, 2015, 92 : 1 - +
  • [28] Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation
    Butcher, Trevor W.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13125 - 13129
  • [29] Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols
    Lafrance, Marc
    Roggen, Markus
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3470 - 3473
  • [30] Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions
    Wu, Yujuan
    Yang, Dingqiao
    Long, Yuhua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (10) : 1522 - 1532