1520942-76-0Relevant articles and documents
A concise cross-metathesis route to enantiopure 1-azaspirocycle S
Wang, Zhen James,Spiccia, Nicolas Daniel,Gartshore, Christopher James,Illesinghe, Jayamini,Jackson, William Roy,Robinson, Andrea Jane
, p. 3118 - 3124 (2013/12/04)
A concise synthesis of spiropyrrolidines and spiropiperidines has been developed. The approach employs a ruthenium-alkylidene-catalysed cross-metathesis reaction of enantiopure N-protected allylglycine with methylenecycloalkanes. The resultant alkene intermediates can then undergo a tandem acid-catalysed cyclisation to form spiropyrrolidines. Ring expansion of the spiropyrrolidine system, via an aziridinium intermediate, grants access to the homologous spiropiperidine ring system with excellent stereoretention. Georg Thieme Verlag Stuttgart New York.