A Concise Cross-Metathesis Route to Enantiopure 1-Azaspirocycles

作者:Wang Zhen James*; Spiccia Nicolas Daniel; Gartshore Christopher James; Illesinghe Jayamini; Jackson William Roy; Robinson Andrea Jane
来源:Synthesis (Germany), 2013, 45(22): 3118-3124.
DOI:10.1055/s-0033-1338527

摘要

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.

  • 出版日期2013-11-18