Chiral Phosphoric Acid Catalyzed Cascade Asymmetric Allylboration/Oxa-Cyclization of Aldehydes for Access to Multisubstituted Tetrahydrofurans

被引：0
|
作者：
Li, Zihan [1 ]
Li, Yichao [1 ]
Zhang, Ruihao [1 ]
Wang, Yuhao [1 ]
Wang, Yilong [1 ]
Yi, Ziqi [2 ]
Huang, Yiyong [1 ]
机构：
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Dept Chem, Wuhan 430070, Peoples R China
[2] Shanghai Univ Engn Sci, Sch Chem & Chem Engn, Shanghai 201210, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2025年
基金：
中国国家自然科学基金;
关键词：
substituted tetrahydrofurans; chiral phosphoric acid; cascade reaction; allylboration; oxa-cyclization; ENANTIOSELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; ALLYLATION;
D O I：
10.1055/a-2513-1926
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optically pure homoallylic alcohols, important synthons fornatural products and bioactive compounds, can be assembled by a chi-ral phosphoric acid catalyzed asymmetric allylboration of aldehydes.Based on this reaction, two unprecedented cascade reactions of func-tionalized aldehydes (allylation/oxa-Michael or oxa-Pictet-Spengler re-actions) for the synthesis of chiral 2,5-disubstituted and 2,2,5-trisubsti-tuted tetrahydrofurans using a single chiral phosphoric acid catalysthave been developed. The reaction mechanism proposed here of theoxa-Pictet-Spengler reaction was investigated through control experiments
引用
收藏
页数：13
相关论文
共 50 条
  • [1] Modular assembly of chiral multisubstituted tetrahydropyrans through a cascade asymmetric aldehyde allylboration/oxa-cyclization by a chiral phosphoric acid
    Wang, Yu-Hao
    He, Bo-Jun
    Kalita, Subarna Jyoti
    Zhao, Zhen-Ni
    Li, Yi-Chao
    Zhang, De-Hua
    Yi, Zi-Qi
    Schneider, Uwe
    Huang, Yi-Yong
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (03): : 838 - 848
  • [2] Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization
    Sun, Huai-Ri
    Zhao, Qingyang
    Yang, Hui
    Yang, Sen
    Gou, Bo-Bo
    Chen, Jie
    Zhou, Ling
    ORGANIC LETTERS, 2019, 21 (17) : 7143 - 7148
  • [3] ASYMMETRIC CYCLIZATION OF UNSATURATED ALDEHYDES CATALYZED BY A CHIRAL LEWIS ACID
    SAKANE, S
    MARUOKA, K
    YAMAMOTO, H
    TETRAHEDRON LETTERS, 1985, 26 (45) : 5535 - 5538
  • [4] ASYMMETRIC CYCLIZATION OF UNSATURATED ALDEHYDES CATALYZED BY A CHIRAL LEWIS ACID
    SAKANE, S
    MARUOKA, K
    YAMAMOTO, H
    TETRAHEDRON, 1986, 42 (08) : 2203 - 2209
  • [5] Chiral Phosphoric Acid-Catalyzed Enantio- and Diastereoselective Allylboration of Aldehydes with β,γ-Substituted Allylboronates
    Yuan, Jinping
    Jain, Pankaj
    Antilla, Jon C.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12): : 8256 - 8266
  • [6] Mechanistic Insights into the BINOL-Derived Phosphoric Acid-Catalyzed Asymmetric Allylboration of Aldehydes
    Grayson, Matthew N.
    Pellegrinet, Silvina C.
    Goodman, Jonathan M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2716 - 2722
  • [7] Chiral Bronsted Acid-Catalyzed Allylboration of Aldehydes
    Jain, Pankaj
    Antilla, Jon C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 11884 - 11886
  • [8] Chiral Bronsted acid-catalyzed allylboration of aldehydes
    Jain, Pankaj
    Antilla, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [9] Aromatic Amine and Chiral Phosphoric Acid Synergistic Catalyzed Cascade Reaction of Alkynylnaphthols with Aldehydes
    Wang, Chuan-Jin
    Meng, Hao-Jie
    Tang, Yue
    Chen, Jie
    Zhou, Ling
    ORGANIC LETTERS, 2024, 26 (07) : 1489 - 1494
  • [10] Chiral Phosphoric Acid Catalyzed Enantioselective Allylation of Aldehydes with Allyltrichlorosilane
    Cheng Ke
    Fan Tiantian
    Sun Jian
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (08) : 1669 - 1671
12345