Jachak, Santosh M. ; Karche, Navnath P. ; Dhavale, Dilip D. (2001) [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 Tetrahedron Letters, 42 (29). pp. 4925-4928. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4039(01)00877-2
Abstract
The reaction of hemiacetal 2a, from the sugar derived α,β-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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Nitrones; Cycloadditions; Cyclitols; Isoxazolidines; Enzyme Inhibitors; Glycosidation |
| ID Code: | 9482 |
| Deposited On: | 02 Nov 2010 12:07 |
| Last Modified: | 01 Jun 2011 10:34 |
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