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
  • [31] Synthesis of novel chiral tetraaza ligands and their application in enantioselective transfer hydrogenation of ketones
    Yu, Shen Luan
    Li, Yan Yun
    Dong, Zhen Rong
    Gao, Jing Xing
    CHINESE CHEMICAL LETTERS, 2012, 23 (04) : 395 - 398
  • [32] Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis-Hillman reactions
    Periasamy, Mariappan
    Gurubrahamam, Ramani
    Muthukumaragopal, Gopal P.
    TETRAHEDRON-ASYMMETRY, 2013, 24 (9-10) : 568 - 574
  • [33] Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles
    He, Yu-Ping
    Wu, Hua
    Wang, Qian
    Zhu, Jieping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (05) : 2105 - 2109
  • [34] Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α, α-difluoro Carbonyl Compounds
    Kashikura, Wataru
    Mori, Keiji
    Akiyama, Takahiko
    ORGANIC LETTERS, 2011, 13 (07) : 1860 - 1863
  • [35] Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (-)-Debromoflustramine B
    Zhang, Zuhui
    Antilla, Jon C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (47) : 11778 - 11782
  • [36] Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis
    Wang, Lei
    Rahman, Abdul
    Lin, Xufeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (28) : 6033 - 6041
  • [37] Continuous-Flow Chemoenzymatic Enantioselective Synthesis of Chiral α-Mono- and Difluoromethyl Amines
    Huang, Chen
    Liu, Yunting
    Kong, Weixi
    Liu, Guanhua
    Zhou, Liya
    He, Ying
    Gao, Jing
    Jiang, Yanjun
    ACS CATALYSIS, 2023, 13 (19) : 12960 - 12969
  • [38] Organocatalytic asymmetric tandem reaction for the enantioselective synthesis of chiral oxindoles to construct CyK dyes
    Wang, Le
    Li, Zi-Hao
    Wu, Di
    Ge, Rui-Tian
    Zhou, Jia
    Zhang, Yin-Feng
    Zhang, Shu-Yu
    CHEM CATALYSIS, 2025, 5 (02):
  • [39] Enantioselective Synthesis of Tetrahydroindolizines via Ruthenium-Chiral Phosphoric Acid Sequential Catalysis
    Zhou, Yong
    Liu, Xiao-Wei
    Gu, Qing
    You, Shu-Li
    SYNLETT, 2016, 27 (04) : 586 - 590
  • [40] Enantioselective organocatalytic synthesis of the chiral chromenes by domino oxa-Michael-aldol reaction
    Pendalwar, Shrikant S.
    Chakrawar, Avinash, V
    Bhusare, Sudhakar R.
    CHINESE CHEMICAL LETTERS, 2018, 29 (06) : 942 - 944
12345