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Intramolecular nitrone dipolar cycloadditions: control of regioselectivity and synthesis of naturally-occurring spirocyclic alkaloids

โœ Scribed by Hodges, Alastair J.; Adams, Joseph P.; Bond, Andrew D.; Holmes, Andrew B.; Press, Neil J.; Roughley, Stephen D.; Ryan, John H.; Saubern, Simon; Smith, Catherine J.; Turnbull, Michael D.; Newton, Annabella F.


Book ID
118150622
Publisher
Royal Society of Chemistry
Year
2012
Tongue
English
Weight
651 KB
Volume
10
Category
Article
ISSN
1477-0520

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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