Rhodium-catalyzed regio- and enantioselective allylic alkylation of pyrazol-5-ones with alkynes

被引：15
|
作者：
Ji, Ding-Wei [1 ,2 ]
Yang, Fan [1 ]
Chen, Bing-Zhi [1 ,2 ]
Min, Xiang-Ting [1 ,2 ]
Kuai, Chang-Sheng [1 ]
Hu, Yan-Cheng [1 ]
Chen, Qing-An [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 60期
基金：
中国国家自然科学基金;
关键词：
C-C; PRIMARY ALCOHOLS; TERMINAL ALKYNES; PALLADIUM; ALLYLATION; ACID; REGIOSELECTIVITY; HYDROAMINATION; INDOLES; KETONES;
D O I：
10.1039/d0cc04002a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A rhodium-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with internal alkynes is illustrated. In the presence of a chiral rhodium-hydride catalyst, functionalized heterocyclic products bearing an all-carbon quaternary stereogenic center were obtained in high yields with satisfactory enantioselectivities. This protocol also features good regiocontrol and a high atom economy without stoichiometric by-product formation.
引用
收藏
页码：8468 / 8471
页数：4
相关论文
共 50 条
  • [31] Rh(I)/Bisoxazolinephosphine-Catalyzed Regio- and Enantioselective Allylic Substitutions
    Xu, Wen-Bin
    Ghorai, Samir
    Huang, Wenyu
    Li, Changkun
    ACS CATALYSIS, 2020, 10 (08): : 4491 - 4496
  • [32] Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides
    Katcher, Matthew H.
    Sha, Allen
    Doyle, Abigail G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (40) : 15902 - 15905
  • [33] Rhodium-Catalyzed Alkylation of Aromatic Ketones with Allylic Alcohols and α,β-Unsaturated Ketones
    Li, Wan-Di
    Zhang, Jia-Shuo
    Zhang, Lin-Yan
    Liu, Zhong-Wen
    Fan, Juan
    Shi, Xian-Ying
    CATALYSTS, 2023, 13 (08)
  • [34] Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers
    Wright, Timothy B.
    Evans, P. Andrew
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (47) : 15303 - 15306
  • [35] Palladium-catalyzed regio- and diastereoselective allylic alkylation with azlactones using triphenylarsine
    Kawatsura, Motoi
    Ikeda, Daiji
    Ishii, Tamiko
    Komatsu, Yuji
    Uenishi, Junichi
    SYNLETT, 2006, (15) : 2435 - 2438
  • [36] Iridium-Catalyzed, Regio- and Enantioselective Allylic Substitution with Aromatic and Aliphatic Sulfinates
    Ueda, Mitsuhiro
    Hartwig, John F.
    ORGANIC LETTERS, 2010, 12 (01) : 92 - 94
  • [37] Rhodium-Catalyzed C-H Alkylation of Indolines with Allylic Alcohols: Direct Access to β-Aryl Carbonyl Compounds
    Han, Sang Hoon
    Choi, Miji
    Jeong, Taejoo
    Sharma, Satyasheel
    Mishra, Neeraj Kumar
    Park, Jihye
    Oh, Joa Sub
    Kim, Woo Jung
    Lee, Jong Suk
    Kim, In Su
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 11092 - 11099
  • [38] Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization
    Chen, Ye-Wei
    Liu, Yang
    Lu, Han-Yu
    Lin, Guo-Qiang
    He, Zhi-Tao
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [39] Organocatalytic Regio- and Enantioselective Allylic Alkylation of Indolin-2-imines with MBH Carbonates toward 3-Allylindoles
    Chen, Lunfeng
    Li, Pengfei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (12) : 7810 - 7814
  • [40] Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes
    Duan, Chang-Lin
    Tan, Yun-Xuan
    Zhang, Jun-Li
    Yang, Shiping
    Dong, Han-Qing
    Tian, Ping
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2019, 21 (06) : 1690 - 1693
12345