A General Method for the Enantioselective Synthesis of α-Chiral Heterocycles

被引：63
|
作者：
Le, Phong Q. [1 ]
Nguyen, Thien S. [1 ]
May, Jeremy A. [1 ]
机构：
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 23期
关键词：
ASYMMETRIC CONJUGATE ALKENYLATION; ACYL IMINES; ARYLBORONIC ACIDS; ENONES; ALLYLBORATION; BIPHENOLS; KETONES; INDOLES; DIOLS; 1,4-ADDITION;
D O I：
10.1021/ol3030605
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective formation of stereocenters proximal to unprotected heterocycles has been accomplished. Thus, vinyl boronic acids are added to heterocycle-appended enones via a modified-BINOL catalyst. Catalyst design was key to enable a general reaction. High yields and useful er's are observed for a host of common heteroaryls.
引用
收藏
页码：6104 / 6107
页数：4
相关论文
共 50 条
  • [41] Application of Rh(I)/Bicyclo[2.2.1]heptadiene Catalysts to the Enantioselective Synthesis of Chiral Amines
    Cheng, Yu-Yi
    Li, Wei-Sian
    Wu, Hsyueh-Liang
    CHEMICAL RECORD, 2021, 21 (12) : 3954 - 3963
  • [42] Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry
    Shi, Yongjie
    Rong, Nianxin
    Zhang, Xumu
    Yin, Qin
    SYNTHESIS-STUTTGART, 2023, 55 (07): : 1053 - 1068
  • [43] Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation
    Liu, Youran
    Chen, Fei
    He, Yan-Mei
    Li, Chenghao
    Fan, Qing-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 5099 - 5105
  • [44] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines
    Boezio, AA
    Charette, AB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) : 1692 - 1693
  • [45] Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines
    Kim, You-Ri
    Hall, Dennis G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) : 4739 - 4748
  • [46] Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel-Crafts Reactions
    Zhuo, Ming-Hua
    Jiang, Yi-Jun
    Fan, Yan-Sen
    Gao, Yang
    Liu, Song
    Zhang, Suoqin
    ORGANIC LETTERS, 2014, 16 (04) : 1096 - 1099
  • [47] Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
    Nimmagadda, Sri Krishna
    Mallojjala, Sharath Chandra
    Woztas, Lukasz
    Wheeler, Steven E.
    Antilla, Jon C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2454 - 2458
  • [48] Enantioselective Organocatalytic Reduction of β-Trifluoromethyl Nitroalkenes: An Efficient Strategy for the Synthesis of Chiral β-Trifluoromethyl Amines
    Massolo, Elisabetta
    Benaglia, Maurizio
    Orlandi, Manuel
    Rossi, Sergio
    Celentano, Giuseppe
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (09) : 3589 - 3595
  • [49] Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes
    Parhi, Biswajit
    Gurjar, Jitendra
    Pramanik, Suman
    Midya, Abhisek
    Ghorai, Prasanta
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) : 4654 - 4663
  • [50] Catalytic Enantioselective Hydrogenation of N-Alkoxycarbonyl Hydrazones: A Practical Synthesis of Chiral Hydrazines
    Yoshikawa, Naoki
    Tan, Lushi
    McWilliams, J. Christopher
    Ramasamy, Deepa
    Sheppard, Ruth
    ORGANIC LETTERS, 2010, 12 (02) : 276 - 279
12345