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
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] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS
    COREY, EJ
    YU, CM
    LEE, DH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 878 - 879
  • [42] General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling
    Li, Bowen
    Aliyu, Muinat
    Gao, Zhenhua
    Li, Tiejun
    Dong, Wei
    Li, Junchen
    Shi, Enxue
    Tang, Wenjun
    ORGANIC LETTERS, 2020, 22 (13) : 4974 - 4978
  • [43] NOVEL AND GENERAL METHOD OF SYNTHESIS OF 2-SUBSTITUTED SELENIUM AND TELLURIUM HETEROCYCLES
    CAGNIANT, D
    KIRSCH, G
    CLOSE, R
    CAGNIANT, P
    CHEMICA SCRIPTA, 1975, A 8 : 113 - 113
  • [44] Progress on the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes
    Wang, Zi-Lu
    Xu, Yun-He
    SYNTHESIS-STUTTGART, 2024, 56 (08): : 1259 - 1272
  • [45] Recent advances in the enantioselective synthesis of chiral drugs
    Juaristi, E
    ANALES DE QUIMICA, 1997, 93 (02): : 135 - 142
  • [46] Renewable Chiral Auxiliary for Enantioselective Synthesis of α-aminoacids
    Rosca, Sorin I.
    Ott, Cristna
    Stan, Raluca
    Raicopol, Matei
    Chiper, Manuela
    REVISTA DE CHIMIE, 2010, 61 (08): : 750 - 754
  • [47] Catalytic enantioselective synthesis of axially chiral allenes
    Ogasawara, Masamichi
    TETRAHEDRON-ASYMMETRY, 2009, 20 (03) : 259 - 271
  • [48] Catalytic Enantioselective Synthesis of Planar Chiral Cyclophanes
    Tanaka, Ken
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (02) : 187 - 194
  • [49] Enantioselective synthesis of β-lactams using a chiral auxiliary
    Yuan, Qing
    Jian, Shan-Zhong
    Wang, Yan-Guang
    SYNLETT, 2006, (07) : 1113 - 1115