Tetrahedron

Ring opening with kinetic resolution of azlactones by Ti-TADDOLates

K Gottwald, D Seebach

Index: Gottwald, Konstanze; Seebach, Dieter Tetrahedron, 1999 , vol. 55, # 3 p. 723 - 738

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Citation Number: 92

Abstract

The kinetic resolution of azlactones by the Lewis-acid-mediated transfer of an isopropoxide ligand from the chiral ligand sphere of Ti-TADDOLate is described. The reactions proceed with in-situ racemization of the starting material to afford highly enantiomerically enriched N- benzoyl-amino acid isopropylesters (er>; 95: 5 after recrystallization). The absolute configuration of the major enantiomer of N-benzoyl-phenylalanine isopropyl ester and its ...