Stereoselective synthesis of chiral oxepanes and pyrans through intramolecular nitrone cycloaddition in organized aqueous media.
[reaction: see text] A highly stereoselective surfactant-catalyzed intramolecular nitrone (formed by dehydration in water) cycloaddition in aqueous media leading to exclusive formation of a single isomer is reported. Either oxepane or pyran is formed from 3-O-allyl furanoside derivatives, which constitute the framework of a large number of biologically active compounds. Therefore, the environmentally friendly, efficient, and highly stereoselective syntheses of these chiral intermediates are still a meaningful pursuit.
Chatterjee
Amrita
A
Chemistry Division, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
Bhattacharya
Pranab K
PK
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D014867:Water
D000447:Aldehydes; D006571:Heterocyclic Compounds; D009589:Nitrogen Oxides; D012997:Solvents; C015388:nitrones; D014867:Water; D006859:Hydrogen