Three-Component Allylic Alkylation Reaction of α-Diazo Ketones with Water and Allyl Carbonates for Construction of Homoallylic Alcohols

被引：0
作者：
Yin, Liping [1 ]
Zhang, Xinyi [2 ]
Wang, Baofan [3 ,4 ]
He, Mingjin [4 ]
Li, Yi [4 ]
Wang, Shaozhen [1 ]
Jing, Tongfei [4 ]
Kang, Zhenghui [2 ,3 ,4 ]
机构：
[1] Wannan Med Coll, Inst Synth & Applicat Med Mat, AnHui Prov Engn Res Ctr Dent Mat & Applicat, Dept Pharm, Wuhu 241002, Peoples R China
[2] Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
[3] Guangzhou Univ Chinese Med, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
[4] Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 17期
基金：
中国博士后科学基金; 中国国家自然科学基金;
关键词：
metal carbene; multicomponent reactions; oxonium ylides; cooperative catalysis; homoallylic alcohols; ENANTIOSELECTIVE SYNTHESIS; DUAL CATALYSIS; CASCADE REACTION; ACID; ALDEHYDES; PYRAZOL-5-ONES; DERIVATIVES; IRIDIUM; YLIDES; ESTERS;
D O I：
10.1002/adsc.202400364
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A three-component allylic alkylation reaction of alpha-diazo ketones, water and allyl carbonate under the cooperative catalysis of Rh2(OAc)4, Pd2(dba)3 and Br & oslash;nsted acid was disclosed. This method provides an expeditious access to alpha-keto homoallylic alcohols in good to high yields. Controlled experiments support that the transformations proceed through cross-interception of two active intermediates Pd-allyl species and enol intermediates derived from oxonium ylides. Moreover, synthetic transformations of the generated products enable the creation of motifs enriched with dense functional groups, underscoring their potential as valuable building blocks. image
引用
收藏
页码：3616 / 3623
页数：8
相关论文
共 84 条
  • [41] Highly Enantioselective Allylic C-H Alkylation of Terminal Olefins with Pyrazol-5-ones Enabled by Cooperative Catalysis of Palladium Complex and Bronsted Acid
    Lin, Hua-Chen
    Wang, Pu-Sheng
    Tao, Zhong-Lin
    Chen, Yu-Gen
    Han, Zhi-Yong
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (43) : 14354 - 14361
  • [42] Dirhodium(II)/Xantphos-Catalyzed Relay Carbene Insertion and Allylic Alkylation Process: Reaction Development and Mechanistic Insights
    Lu, Bin
    Liang, Xinyi
    Zhang, Jinyu
    Wang, Zijian
    Peng, Qian
    Wang, Xiaoming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (30) : 11799 - 11810
  • [43] Total Synthesis of Aplysiasecosterol A
    Lu, Zhaohong
    Zhang, Xiang
    Guo, Zhicong
    Chen, Yu
    Mu, Tong
    Li, Ang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (29) : 9211 - 9218
  • [44] Synthesis and Characterization of Donor-Acceptor Iron Porphyrin Carbenes and Their Reactivities in N-H Insertion and Related Three- Component Reaction
    Ma, Chaoqun
    Wang, Shang
    Sheng, Yuan
    Zhao, Xiao-Li
    Xing, Dong
    Hu, Wenhao
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (09) : 4934 - 4939
  • [45] α-Quaternary Chiral Aldehydes from Styrenes, Allylic Alcohols, and Syngas via Multi-catalyst Relay Catalysis
    Meng, Jing
    Fang, Lian-Feng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    [J]. CHEM, 2018, 4 (05): : 1047 - 1058
  • [46] Chiral counteranions in asymmetric transition-metal catalysis:: Highly enantioselective Pd/Bronsted acid-catalyzed direct α-allylation of aldehydes
    Mukherjee, Santanu
    List, Benjamin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (37) : 11336 - +
  • [47] Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides
    Nair, Vaishnavi N.
    Kojasoy, Volga
    Laconsay, Croix J.
    Kong, Wang Yeuk
    Tantillo, Dean J.
    Tambar, Uttam K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (24) : 9016 - 9025
  • [48] Total Syntheses of Thailanstatins A-C, Spliceostatin D, and Analogues Thereof. Stereodivergent Synthesis of Tetrasubstituted Dihydro- and Tetrahydropyrans and Design, Synthesis, Biological Evaluation, and Discovery of Potent Antitumor Agents
    Nicolaou, K. C.
    Rhoades, Derek
    Kumar, S. Mothish
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (26) : 8303 - 8320
  • [49] Otera J., 2000, MODERN CARBONYL CHEM, P299
  • [50] Palladium-Catalyzed Three-Component Selective Aminoallylation of Diazo Compounds
    Ou, Pengcheng
    Zhu, Lei
    Yu, Yinghua
    Ma, Liyao
    Huang, Xueliang
    [J]. ORGANIC LETTERS, 2022, 24 (23) : 4160 - 4164
123456789