Tetrahedron: Asymmetry

Synthesis of dirhodium (II) tetrakis [methyl 1-(3-phenylpropanoyl)-2-oxaimidazolidine-4 (S)-carboxylate], Rh 2 (4S-MPPIM) 4

MP Doyle, JT Colyer

Index: Doyle, Michael P.; Colyer, John T. Tetrahedron Asymmetry, 2003 , vol. 14, # 22 p. 3601 - 3604

Full Text: HTML

Citation Number: 14

Abstract

The large-scale synthesis with greatly improved yields of methyl 1-(3-phenylpropanoyl)-2- oxaimidazolidine-4 (S)-carboxylate and the chiral dirhodium (II) carboxamidate derived from it, Rh2 (4S-MPPIM) 4, is described. The key step in the overall synthesis is the Hofmann rearrangement of Boc-protected l-asparagine, the procedure for which has been modified to achieve near quantitative yield.