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  • Title: Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose: diastereoselective ether formation.
    Author: Sacui IA, Zeller M, Norris P.
    Journal: Carbohydr Res; 2008 Jul 21; 343(10-11):1819-23. PubMed ID: 18439572.
    Abstract:
    Standard diazo transfer to 3-O-(2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-d-allofuranose (2), using p-acetamidobenzenesulfonyl azide (p-ABSA, 3) and DBU as base, provides the expected 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (4) as an orange syrup in 49% isolated yield. Subsequent decomposition of 4 using Rh(2)(OAc)(4) yields ether 5 in a highly diastereoselective manner and in 58% isolated yield. The X-ray crystal structure of 5 proves that both newly produced stereocenters have the (S) configuration; the conformation of the ester group at O-3 of the furanose ring of 5 is used to discuss the possible cause of the observed stereoselectivity.
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