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Synthesis of 2,4-methanoproline analogues via an addition-intramolecular substitution sequence
Thomas Rammeloo1, Christian V Stevens, Norbert De Kimpe
1Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, B-9000 Gent, Belgium.
The Journal of Organic Chemistry
|August 31, 2002
Abstract:
A new two-step synthetic approach toward 3-(chloromethyl)cyclobutanone is described and used in the synthesis of 2,4-methanoproline analogues. The key step consists of a reversible addition of hydrogen cyanide onto the imines 12 in 50-74% yield under conditions that allow ring closure. 2-Alkyl-2-azabicyclo[2.1.1]hexane-1-carbonitriles 19, synthesized in four steps, can also be converted to the corresponding amines.