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Gold(I) Catalysis: Selective Synthesis of Six‐ or Seven‐Membered Heterocycles from Epoxy Alkynes
Author(s) -
Dai LunZhi,
Shi Min
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900210
Subject(s) - cycloisomerization , chemistry , ketone , intramolecular force , isomerization , lewis acids and bases , nucleophile , alkyne , catalysis , organic chemistry , hydroamination , medicinal chemistry
Gold(I)‐catalyzed intramolecular cycloisomerization of ketone‐substituted epoxides with alkynes to six‐ or seven‐membered heterocyclic compounds is firstly introduced in this paper. This procedure involves a cascade isomerization of the ketone‐substituted epoxides into 1,3‐diketones in the presence of a Lewis acid and subsequent gold(I)‐catalyzed selective intramolecular addition of an oxygen or a carbon nucleophile to the alkynes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)