Conversion of Thio- And Selenophosphoryl into Phosphoryl Group by Perfluoro cis-2,3-Dialkyloxaziridines

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6401-6403

  Arnone, Alberto ^a   Novo, Barbara ^a   Pregnolato, Massimo ^b   Resnati, Giuseppe ^a   Terreni, Marco ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011634422     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970572a     Document Type: Article

References (50)

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14. The (2S,4R,5S) configuration was assigned to the product 3n obtained by oxidizing (2S,4R,5S)-2n with oxaziridines 1a,b as no NOE was observed in this diastereoisomer between the methyl on C-4 and the methylene and aromatic protons of the benzylamido residue. This observation suggested that the two groups are trans. In order to confirm this assignment, (2S,4R,5S)-2n was oxidized with MCPBA. This reagent is known to perform the oxidative desulfurization reaction with retention of chirality on 2-(methylthio)-1,3,2-oxazaphospholidine 2-sulfides (ref 10a), phosphonamidothioates (ref 10b), phosphinothioates (ref 10c), and phosphorothioates (ref 10d) and in fact a different 1,3,2-oxazaphospholidine 2-oxide 3n was formed which showed positive NOE effects between the above described residues (see the Experimental Section). These residues were thus in a cis relationship, and the (2A,4R,5S) configuration could be assigned unequivocally to this product.
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