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Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems
Pratik Kumar1, Omar Zainul, Scott T Laughlin
1Department of Chemistry, Stony Brook University, Stony Brook, New York 11794, USA.
Abstract:
Cyclic enamines are important synthons for many synthetic and pharmacological targets. Here, we report an inexpensive, catalyst-free, multigram-scale synthesis for cyclic enamines with exocyclic double bonds and four- to seven-membered rings. This strategy is more conducive to scale up, permissive of functionalization around the cyclic system, and less sensitive to the nature of the N-protecting group than previously-described methods for cyclic enamine synthesis. Further, we explore application of these enamines to the synthesis of highly-strained spirocyclic 3N-cyclopropyl scaffolds.
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