Synthesis of 2,4-methanoproline analogues via an addition-Intramolecular substitution sequence
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.
Rammeloo, Thomas,Stevens, Christian V.,De Kimpe, Norbert
p. 6509 - 6513
(2007/10/03)
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