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Synthesis of trihydroxy quinolizidine alkaloids: 1,3-addition reaction of allylmagnesium bromide to a sugar nitrone

โœ Scribed by Dilip D Dhavale; Santosh M Jachak; Navnath P Karche; Claudio Trombini


Book ID
108282516
Publisher
Elsevier Science
Year
2004
Tongue
French
Weight
216 KB
Volume
60
Category
Article
ISSN
0040-4020

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[1,3]-Dipolar intramolecular nitrone ole
โœ Santosh M Jachak; Navnath P Karche; Dilip D Dhavale ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 92 KB

The reaction of hemiacetal 2a, from the sugar derived a,b-unsaturated ester 1a, with N-benzylhydroxylamine hydrochloride in situ generates an N-benzylnitrone as a 1,3-dipole, which spontaneously undergoes diastereo-and regioselective intramolecular nitrone olefin cycloaddition to afford a hydroxy fu