The reactions of α-chalcogen, α-halo, or
α-amino
functionally substituted enals with terminal alkynes leading either
to corresponding propargyl alcohols (for O-, S-, Cl-, and Br-bearing
substrates) or unexpected 2-amino-2-cyclopentenones (for aminoenals)
are described. The key feature of these reactions is the rearrangement
of adducts bearing amino groups on silica gel that triggered further
cyclization to five-membered carbocycles.
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