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$\left[Zn(OTf)_{2}\right]$-catalyzed synthesis of 2-alkynylazetidines and their ring expansion to functionalized 1,4,5,6-tetrahydropyridines

Tijdschriftbijdrage - Tijdschriftartikel

A zinc(II) triflate catalyzed reaction of beta-chloro aldimines with terminal alkynes leading to a rapid and efficient formation of 2-alkynylazetidines in good to excellent yield has been described. The catalytic hydrogenation of the 2-alkynylazetidines resulted in acyclic secondary amines by reductive cleavage of the 2-alkynylazetidine. Further, these non-activated 2-alkynylazetidines were ring expanded in a reaction with dimethyl acetylenedicarboxylate in the presence of zinc(II) triflate to give 4-alkynyltetrahydropyridines. Catalytic reduction of these 4-alkynyltetrahydropyridines led to an efficient conversion to 4-alkyltetrahydropyridine carboxylates.
Tijdschrift: Advanced synthesis and catalysis
ISSN: 1615-4150
Volume: 360
Pagina's: 4393 - 4401
Jaar van publicatie:2018
Trefwoorden:A1 Journal article
BOF-keylabel:ja
BOF-publication weight:10
CSS-citation score:1
Authors from:Higher Education
Toegankelijkheid:Closed