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Title
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-catalyzed synthesis of 2-alkynylazetidines and their ring expansion to functionalized 1,4,5,6-tetrahydropyridines
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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Advanced synthesis and catalysis. - Weinheim, 2001, currens
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Publication
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Weinheim
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2018
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ISSN
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1615-4150
[print]
1615-4169
[online]
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DOI
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10.1002/ADSC.201800932
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Volume/pages
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360
:22
(2018)
, p. 4393-4401
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ISI
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000450364400016
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Full text (Publisher's DOI)
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