✦ LIBER ✦
[1,3]-Dipolar intramolecular nitrone olefin cycloaddition reaction of a sugar-derived α,β-unsaturated ester: a new diastereo- and regioselective synthesis of an aminocyclopentitol
✍ Scribed by Santosh M Jachak; Navnath P Karche; Dilip D Dhavale
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 92 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 functionalised 4-exo-ethoxycarbonyl-3-oxa-2-azabicyclo[3.3.0]octane system, a precursor to a hitherto unknown aminocyclopentitol derivative.