title: N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine.
abstract: [reaction: see text] N-Sulfinyl beta-amino Weinreb amides are prepared by condensation of sulfinimines with the potassium enolate of N-methoxy-N-methylacetamide. These new chiral building blocks are useful for the asymmetric synthesis of beta-amino carbonyl compounds, as illustrated here by the concise enantioselective syntheses of sedum alkaloids (+)-sedridine and (-)-allosedridine.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
authors.forename: M Brad
authors.initials: MB
authors.lastname: Nolt
authors.forename: Yongzhong
authors.initials: Y
authors.lastname: Wu
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis*
chemical_list: D000577:Amides; D007202:Indicators and Reagents; D010880:Piperidines; D013454:Sulfoxides; C011350:sedridine