Lewis Base-Catalyzed One-Pot Cascade Sequences of O-Alkenyl-Substituted Cyanohydrins: Diastereoselective Synthesis of Multisubstituted Dihydrofurans

被引:8
|
作者
Du, Shan-Tao [1 ]
Sun, Zhen [1 ]
Liu, Wei [1 ]
Liao, Wei-Wei [1 ]
机构
[1] Jilin Univ, Coll Chem, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China
关键词
QUATERNARY CARBON CENTERS; FREE INTRAMOLECULAR CARBOCYANATION; ORGANOCATALYTIC DOMINO REACTIONS; ASYMMETRIC-SYNTHESIS; ACTIVATED ALKENES; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; CONSTRUCTION; 2,3-DIHYDROBENZOFURANS; ACYLCYANATION;
D O I
10.1021/acs.orglett.7b03301
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of the diastereoselective construction of polysubstituted 2,3-dihydrofurans incorporating contiguous quaternary and tertiary carbon centers via a Lewis base-catalyzed one-pot cascade sequence is described. The diversity and complexity of the final products can be efficiently constructed with high diastereoselectivities via this catalytic multistep process under mild reaction conditions.
引用
收藏
页码:6598 / 6601
页数:4
相关论文
共 50 条
  • [1] One-Pot Synthesis of Substituted Di-Hydrofurans from Lewis Base-Catalyzed Three-Component Condensation
    Zhong, Cheng
    Liao, Tao
    Tuguldur, Odbadrakh
    Shi, Xiaodong
    ORGANIC LETTERS, 2010, 12 (09) : 2064 - 2067
  • [2] Base-Catalyzed One-Pot Synthesis of 2,3,6-Substituted Pyridines
    Zhu, Baofu
    He, Jiaming
    Zou, Kai
    Li, Anquan
    Zhang, Chen
    Zhao, Jiaji
    Cao, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11450 - 11459
  • [3] Base-Catalyzed One-Pot Synthesis of Selenosulfides: A Base Basicity-Controlled Approach
    Lee, Sangik
    Sim, Jaehee
    Lee, Anna
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 748 - 755
  • [4] Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
    Elkamhawy, Ahmed
    Jaragh-Alhadad, Laila
    Mekheimer, Ramadan Ahmed
    Abdullah, Omeima
    Abd-Elmonem, Mohamed
    Moustafa, Moustafa Sherief
    Abdel-Hameed, Afaf
    Mohamed, Tahany Mahmoud
    Sadek, Kamal Usef
    GREEN PROCESSING AND SYNTHESIS, 2023, 12 (01)
  • [5] Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles
    Schmidt, Elena Yu
    Ivanova, Elena V.
    Semenova, Nadezhda V.
    Tatarinova, Inna V.
    Ushakov, Igor A.
    Trofimov, Boris A.
    MENDELEEV COMMUNICATIONS, 2015, 25 (02) : 131 - 132
  • [6] Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One-Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols
    Xu, Xinfang
    Han, Xingchun
    Yang, Liping
    Hu, Wenhao
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) : 12604 - 12607
  • [7] One-pot cascade Michael-Michael-Aldol condensation for diastereoselective synthesis of nitro-substituted cyclohexanes
    Chen, Yunfeng
    Zhong, Cheng
    Sun, Xiaohua
    Akhmedov, Novruz G.
    Petersen, Jeffrey L.
    Shi, Xiaodong
    CHEMICAL COMMUNICATIONS, 2009, (34) : 5150 - 5152
  • [8] One-pot synthesis of β-lactams from aldimines and ketene silyl acetats by tandem Lewis base-catalyzed Mannich-type addition and cyclization
    Takahashi, E
    Fujisawa, H
    Yanai, T
    Mukaiyama, T
    CHEMISTRY LETTERS, 2005, 34 (02) : 216 - 217
  • [9] Gold(I)-Catalyzed One-Pot and Diastereoselective Synthesis of trans-2-Silyl-4,5-dihydrofurans from Propargylsilanes and Aldehydes
    Fernandez, Sergio
    Santamaria, Javier
    Ballesteros, Alfredo
    ORGANIC LETTERS, 2020, 22 (16) : 6590 - 6594
  • [10] One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of α,β-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate
    Li, Lei
    Chen, Jia-Jia
    Kan, Xing-Lan
    Zhang, Lu
    Zhao, Yu-Long
    Liu, Qun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) : 4892 - 4899