Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems. Issue 4 (5th January 2018)

• Record Type: Journal Article
• Authors: Kumar, Pratik; Zainul, Omar; Laughlin, Scott T.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 4(2017)
• Page Start: 652
• Page End: 656
• Publication Date: 2018-01-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02659e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Cyclic enamines are important synthons for many synthetic and pharmacological targets. We report a method for the synthesis of cyclic enamines with exocyclic double bonds and four- to seven-membered rings that permits usage of common N -protecting groups and tolerates functionality round the ring system. 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.