The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy- 3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.
1,3-Dipolar Cycloadditions of 2-(tert-Butoxycarbonyl)-1-Pyrroline N-Oxide with chiral Acrylates and Acrylamides / F. PISANESCHI; M. SALVATI; M. GENSINI; F. CORDERO; A. BRANDI. - In: HETEROCYCLES. - ISSN 0385-5414. - STAMPA. - 67:(2006), pp. 413-420. [10.3987/COM-05-S(T)37]
1,3-Dipolar Cycloadditions of 2-(tert-Butoxycarbonyl)-1-Pyrroline N-Oxide with chiral Acrylates and Acrylamides
CORDERO, FRANCA MARIA;BRANDI, ALBERTO
2006
Abstract
The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy- 3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.
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