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Synlett 1998; 1998(12): 1444-1446
DOI: 10.1055/s-1998-1940
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Remarkable High-pressure Enhancement of Enantiopure Nitrone Cycloadditions to Glycals: General Access to (1 → 2)-Linked Pseudo Aza-C-disaccharides

Francesca Cardona* , Piotr Salanski, Marek Chmielewski, Silvia Valenza, Andrea Goti, Alberto Brandi
  • *Centro di studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Dipartimento di Chimica Organica "U. Schiff", Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy; Fax 39 55 2 47 69 64; E-mail: goti@chimorg.unifi.it/brandi@chimorg.unifi.it
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Publication Date:
31 December 2000 (online)

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1,3-Dipolar cycloadditions of enantiopure hydroxylated nitrones to glycals are strongly accelerated under high pressure. Under 10 Kbar pressure the process gains generality and broad scope and allows a direct access, in good to excellent yields, to stereodifferentiated tricyclic isoxazolidines, key intermediates for the synthesis of a new class of (1 → 2) linked pseudo aza-C-disaccharides.

high pressure - hydroxylated enantiopure nitrones - 1,3-dipolar cycloaddition - glycals - double stereoinduction