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
  • [1] Does an Enol Pathway Preclude High Stereoselectivity in Iron-Catalyzed Indole C-H Functionalization via Carbene Insertion?
    Balhara, Reena
    Jindal, Garima
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12) : 7919 - 7933
  • [2] Allylsilanes in organic synthesis - Recent developments
    Chabaud, L
    James, P
    Landais, Y
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) : 3173 - 3199
  • [3] Pd(II)/Bronsted Acid Catalyzed Enantioselective Allylic C-H Activation for the Synthesis of Spirocyclic Rings
    Chai, Zhuo
    Rainey, Trevor J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (08) : 3615 - 3618
  • [4] Enantioselective three-component aminomethylation of α-diazo ketones with alcohols and 1,3,5-triazines
    Che, Jiuwei
    Niu, Li
    Jia, Shikun
    Xing, Dong
    Hu, Wenhao
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)
  • [5] Divergent Geminal Alkynylation-Allylation and Acylation-Allylation of Carbenes: Evolution and Roles of Two Transition-Metal Catalysts
    Chen, Hongda
    Yang, Wenhan
    Zhang, Jinyu
    Lu, Bin
    Wang, Xiaoming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (07) : 4727 - 4740
  • [6] Chemo-selective Rh(II)/Pd(0) Dual Catalysis: Synthesis of All-Carbon C3-Quaternary Allylic Oxindoles from N-Aryl-α-Diazo-β-Keto-Amides with Functionalized Allyl Carbonates
    Chen, Ling-Hang
    Ma, Yang-Ting
    Yang, Fang
    Huang, Xiao-Yan
    Chen, Shu-Wei
    Ji, Kegong
    Chen, Zi-Sheng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1307 - 1312
  • [7] Forming All-Carbon Quaternary Centers by Geminal Difunctionalization of Diazo Compounds with N,N-Disubstituted Anilines and Carbonates
    Chen, Qiang
    Huang, Tingzhong
    Shao, Ying
    Tang, Shengbiao
    Sun, Jiangtao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05) : 3308 - 3312
  • [8] Self-emulsifying System Co-loaded with Paclitaxel and Coix Seed Oil Deeply Penetrated to Enhance Efficacy in Cervical Cancer
    Chen, Yunyan
    Wang, Shaozhen
    Hu, Qiyan
    Zhou, Lingyun
    [J]. CURRENT DRUG DELIVERY, 2023, 20 (07) : 919 - 926
  • [9] Three-component chemo-selective oxy-allylation of a-diazo carbonyl compounds: Access to a-ternary carboxylic esters
    Chen, Zi-Sheng
    Huang, Xiao-Yan
    Liu, Qing
    Song, De-Xin
    Yang, Fang
    Ji, Kegong
    [J]. JOURNAL OF CATALYSIS, 2023, 417 : 52 - 59
  • [10] Rh(II)/Pd(0) Dual Catalysis: Regiodivergent Transformations of Alkylic Oxonium Ylides
    Chen, Zi-Sheng
    Huang, Xiao-Yan
    Chen, Ling-Hang
    Gao, Jin-Ming
    Ji, Kegong
    [J]. ACS CATALYSIS, 2017, 7 (11): : 7902 - 7907
123456789