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Gold‐ and Silver‐Catalyzed [4+2] Cycloadditions of Ynamides with Oxetanes and Azetidines
Author(s) -
Pawar Samir Kundlik,
Vasu Dhananjayan,
Liu RaiShung
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400024
Subject(s) - chemistry , oxetane , electrophile , nucleophile , cycloaddition , catalysis , combinatorial chemistry , organic chemistry
Gold‐catalyzed [4+2] cycloadditions between ynamides and oxetanes are described; these reactions involve oxetanes and gold‐π‐ynamides as nucleophiles and electrophiles, respectively. Excellent cycloaddition regioselectivities are achieved over a reasonable range of ynamide and oxetane substrates. For azetidines, their [4+2] cycloadditions with ynamides are implemented more efficiently with silver hexafluoroantimonate, which is also compatible with various ynamides and azetidines. These two cycloadditions provide facile accesses to six‐membered heterocycles such as 6‐amino‐3,4‐dihydro‐2 H ‐pyrans and 2‐amino‐1,4,5,6‐tetrahydropyridines.