Abstract
Olsson’s three-component reaction of cyclopropylketones, aldehydes, and primary amines was investigated for application to parallel synthesis. Using an excess of Et 2AlI at elevated temperatures, pyrrolidines 4 , the initial products reported by Olsson and co-workers, could be completely converted to pyrrolium salts 5 , by a reaction sequence involving a retro-aza-Michael addition followed by iminium salt formation. The pyrrolium salts 5 were then cleanly reduced in situ by NaBH(OAc) 3 to give 3-alkylidenylpyrrolidines 6 . In summary, this one-pot three-component reaction provided an efficient synthetic route to 3-alkylidenylpyrrolidines.
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