N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine.
[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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Prasad
Kavirayani R
KR
Nolt
M Brad
MB
Wu
Yongzhong
Y
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*
D000577:Amides; D007202:Indicators and Reagents; D010880:Piperidines; D013454:Sulfoxides; C011350:sedridine