Tetrahedron

Resolution and use in α-amino acid synthesis of imidazolidinone glycine derivatives

R Fitzi, D Seebach

Index: Fitzi, Robert; Seebach, Dieter Tetrahedron, 1988 , vol. 44, # 17 p. 5277 - 5292

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Citation Number: 177

Abstract

The imidazolidinones (rac.-1 and rac.-2) obtained from pivalaldehyde and glycine amides are resolved efficiently by crystallization of diastereoisomeric ammonium salts with chiral acids (mandelates and a gulonate respectively). The free bases are acylated under Schotten- Baumann conditions to give enantiomerically pure 1-Bz., 1-BOC-, 1-2-or 1-formyl-2-t-butyl-3- methyl-or-3-benzyl-4-imidazolidinones. Diastereoselective alkylation of the 3-methyl ...