Chromium(II)-catalyzed enantioselective arylation of ketones

被引：4
|
作者：
Wang, Gang [1 ,2 ]
Sun, Shutao [2 ]
Mao, Ying [2 ]
Xie, Zhiyu [2 ]
Liu, Lei [1 ,2 ,3 ]
机构：
[1] Shandong Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China
[2] Shandong Univ, Sch Pharmaceut Sci, Jinan 250012, Peoples R China
[3] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷
基金：
美国国家科学基金会;
关键词：
arylation; asymmetric catalysis; chromium; ketone; tertiary alcohol; NOZAKI-HIYAMA ALLYLATION; MEDIATED COUPLING REACTIONS; FREE-ENERGY RELATIONSHIPS; ASYMMETRIC CATALYSIS; ORGANOCHROMIUM REAGENTS; CHROMIUM CATALYSIS; KISHI REACTION; LIGAND; ALDEHYDES; HALIDES;
D O I：
10.3762/bjoc.12.275
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.
引用
收藏
页码：2771 / 2775
页数：5
相关论文
共 50 条
  • [21] Pd-catalyzed enantioselective intramolecular α-arylation of α-substituted cyclic ketones: facile synthesis of functionalized chiral spirobicycles
    Fan, Lulu
    Takizawa, Shinobu
    Takeuchi, Yoshiki
    Takenaka, Kazuhiro
    Sasai, Hiroaki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4837 - 4840
  • [22] Palladium-catalyzed alpha-arylation of ketones
    Palucki, M
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (45) : 11108 - 11109
  • [23] Palladium-Catalyzed Denitrative α-Arylation of Ketones with Nitroarenes
    Li, Zhirong
    Peng, Yonggang
    Wu, Tao
    ORGANIC LETTERS, 2021, 23 (03) : 881 - 885
  • [24] Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives
    Takise, Ryosuke
    Muto, Kei
    Yamaguchi, Junichiro
    Itami, Kenichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (26) : 6791 - 6794
  • [25] Progress in the palladium-catalyzed α-arylation of ketones with chloroarenes
    Ehrentraut, A
    Zapf, A
    Beller, M
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (02) : 209 - 217
  • [26] Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines
    Kato, Naoya
    Shirai, Tomohiko
    Yamamoto, Yasunori
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (23) : 7739 - 7742
  • [27] Palladium-Catalyzed Enantioselective γ-Arylation of β,γ-Unsaturated Butenolides
    Li, Sanliang
    Chen, Qiaoyu
    Yang, Junfeng
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (23)
  • [28] Ni-catalyzed, enantioselective arylation of pyridinium ions
    Lutz, John
    Chau, Stephen
    Doyle, Abigail
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [29] Design and synthesis of modular oxazoline ligands for the enantioselective chromium-catalyzed addition of allyl bromide to ketones
    Miller, Jeremie J.
    Sigman, Matthew S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) : 2752 - +
  • [30] Indolinylmethanol catalyzed enantioselective Reformatsky reaction with ketones
    Lin, Ning
    Chen, Miao-Miao
    Luo, Ren-Shi
    Deng, Yan-Qiu
    Lu, Gui
    TETRAHEDRON-ASYMMETRY, 2010, 21 (23) : 2816 - 2824
12345