Cobalt-Catalyzed Asymmetric Hydrosilylation of ?-Oxygenated Ketones

被引：6
|
作者：
Wen, Huiting [1 ]
Chen, Yifei [1 ]
Shi, Lanxuan [1 ]
Chen, Jianhui [1 ]
Luo, Yanshu [1 ]
Xia, Yuanzhi [1 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 13期
关键词：
ALPHA-HYDROXY KETONES; ENANTIOSELECTIVE HYDROSILYLATION; TRANSFER HYDROGENATION; KINETIC RESOLUTION; 1,2-AMINO ALCOHOLS; TERMINAL EPOXIDES; METAL; IRON; ALKENES; ARYL;
D O I：
10.1021/acs.orglett.3c00162
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric hydrosilylation of alpha-oxygenated ketones was developed under the catalysis of Co(OAc)2 in combination with a chiral phosphine-amido-oxazoline (PAO) ligand, providing a mild, efficient, and enantioselective access to a variety of synthetically useful 1,2-diol derivatives. This protocol can be carried out at the gram scale with a catalyst loading of 1 mol %, and its synthetic utility was demonstrated by efficient conversion of the optically enriched products into chiral alpha-hydroxy acid, 1,3dioxolan-2-one, ethylene oxide, and 1,2,3-1H-triazole.
引用
收藏
页码：2184 / 2189
页数：6
相关论文
共 50 条
  • [31] Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones
    Liu, Wenbo
    Guo, Jun
    Xing, Shipei
    Lu, Zhan
    ORGANIC LETTERS, 2020, 22 (07) : 2532 - 2536
  • [32] Cobalt-Catalyzed Enantioselective Vinylation of Activated Ketones and Imines
    Huang, Yuan
    Huang, Rui-Zhi
    Zhao, Yu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (20) : 6571 - 6576
  • [33] Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins
    Yang, Junfeng
    Yoshikai, Naohiko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (48) : 16748 - 16751
  • [34] Cobalt-catalyzed conjugate addition of silylacetylenes to α,β-unsaturated ketones
    Nishimura, Takahiro
    Sawano, Takahiro
    Ou, Keiyu
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2011, 47 (36) : 10142 - 10144
  • [35] Cobalt-Catalyzed Enantioselective Reductive Amination of Ketones with Hydrazides
    Chen, Tiantian
    Hu, Yanhua
    Tang, Xuyang
    Zou, Yashi
    Wei, Liangming
    Zhang, Zhenfeng
    Zhang, Wanbin
    ORGANIC LETTERS, 2023, 26 (04) : 769 - 774
  • [36] Asymmetric Synthesis of Silicon-Stereogenic Vinylhydrosilanes by Cobalt-Catalyzed Regio- and Enantioselective Alkyne Hydrosilylation with Dihydrosilanes
    Wen, Huanan
    Wan, Xiaolong
    Huang, Zheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (21) : 6319 - 6323
  • [37] Regio-controllable Cobalt-Catalyzed Sequential Hydrosilylation/Hydroboration of Arylacetylenes
    Cheng, Zhaoyang
    Guo, Jun
    Sun, Yufeng
    Zheng, Yushan
    Zhou, Zhehong
    Lu, Zhan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (41) : 22454 - 22460
  • [38] Cobalt-Catalyzed Chemoselective and Divergent Synthesis of Vinylsilanes through Hydrosilylation of Acetylene
    Long, Xianyang
    Zhu, Dong
    Zhu, Shifa
    ACS CATALYSIS, 2025, 15 (06): : 4429 - 4440
  • [39] Cobalt-Catalyzed Asymmetric Synthesis of gem-Bis(silyl)alkanes by Double Hydrosilylation of Aliphatic Terminal Alkynes
    Guo, Jun
    Wang, Hongliang
    Xing, Shipei
    Hong, Xin
    Lu, Zhan
    CHEM, 2019, 5 (04): : 881 - 895
  • [40] Cobalt-Catalyzed Alkyne Hydrosilylation and Sequential Vinylsilane Hydroboration with Markovnikov Selectivity
    Zuo, Ziqing
    Yang, Ji
    Huang, Zheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (36) : 10839 - 10843
12345