Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using delta-amino beta-ketophosphonates and ring-closing metathesis (RCM).
Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry. [reaction: see text]
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. fdavis@temple.edu
Wu
Yongzhong
Y
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism
C496160:4-aminocyclopentenone; D003517:Cyclopentanes; D006844:Hydrocarbons, Cyclic; D007659:Ketones; D009705:Nucleosides; D063065:Organophosphonates; C013905:cyclopentenone