Accessing N‐Propargyl Amino Alcohols through Cu(I)‐Catalyzed A3‐Coupling/Annulation and Bi(III)‐Promoted Ring‐Opening. Issue 7 (17th February 2022)

• Record Type: Journal Article
• Authors: Cao, Leilei; Zhou, Pengyu; Hu, Junduo; Huang, Liliang; Feng, Huangdi
• Is Part Of: ChemistrySelect. Volume 7:Issue 7(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-02-17
• Subjects: Multicomponent reactions -- A3-coupling -- Annulation -- Ring-opening -- Amino alcohols; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202200200
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An efficient one‐pot, two‐step process of N‐propargylation of amino alcohols involving in situ protection and deprotection of the amino alcohols. This reaction is initiated by a Cu(I)‐catalyzed A 3 ‐coupling/annulation of an amino alcohol, formaldehyde solution, and a terminal alkyne. Subsequent Bi(III)‐promoted ring‐opening of oxazolidine intermediates leads to the formation of the corresponding N−H‐free N‐propargyl amino alcohols in moderate to excellent yields. Importantly, this strategy allows a wide range of substrates with good functional group tolerance. Abstract : A novel and practical approach for the synthesis of N−H free N ‐propargyl amino alcohols from amino alcohols, formaldehyde, and alkynes is described via Cu(I)‐catalyzed A 3 ‐coupling/annulation with Bi(III)‐promoted ring‐opening.