A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptan-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-b-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations.
Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]cycloaddidition of N-allyl b-N-keteniimminium salts derived from (R)-vinylglycinol
ZAPPIA, GIOVANNI;
2000
Abstract
A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptan-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-b-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations.File in questo prodotto:
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