Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose: diastereoselective ether formation
In: Carbohydrate Research, Jg. 343 (2008-07-21), Heft 10/11, S. 1819-1823
academicJournal
Zugriff:
Abstract: Standard diazo transfer to 3-O-(2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-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-α-d-allofuranose (4) as an orange syrup in 49% isolated yield. Subsequent decomposition of 4 using Rh2(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. [Copyright &y& Elsevier]
Titel: |
Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-α-d-allofuranose: diastereoselective ether formation
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Autor/in / Beteiligte Person: | Sacui, Iulia A. ; Zeller, Matthias ; Norris, Peter |
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Zeitschrift: | Carbohydrate Research, Jg. 343 (2008-07-21), Heft 10/11, S. 1819-1823 |
Veröffentlichung: | 2008 |
Medientyp: | academicJournal |
ISSN: | 0008-6215 (print) |
DOI: | 10.1016/j.carres.2008.04.005 |
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