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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective synthesis of chiral oxepanes and pyrans through intramolecular nitrone cycloaddition in organized
Amrita Chatterjee1, Pranab K Bhattacharya
1Chemistry Division, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
Abstract:
[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.
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