Facile Preparation of tert-Butyl 1-tert-Butoxycarbonylaminocyclopent-3-enecarboxylate from Inexpensive Starting Materials

Abstract

1,5-C,C-Cycloalkylation of tert-butyl acetoacetate (1) with cis-1,4-dichloro-2-butene (2) followed by the haloform reaction of the product in NaOH solution and subsequent Curtius degradation in tert-butyl alcohol furnished tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate (5) in 32% overall yield.

alkenes - cyclizations - excitatory amino acids - haloform reaction - Curtius rearrangement

References

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