Tetrahedron letters

Asymmetric synthesis of 3S, 4R-dihydroxypyrrolidines by regio-and stereoselective hydroxylation of 4-oxoproline enolate

MJ Blanco, FJ Sardina

Index: Blanco, M. Jesus; Sardina, F. Javier Tetrahedron Letters, 1994 , vol. 35, # 45 p. 8493 - 8496

Full Text: HTML

Citation Number: 33

Abstract

Abstract A short, efficient and stereoselective synthesis of enantiomerically pure (2R, 3S, 4R) 3, 4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L- proline is presented. The key steps are the regio-and stereoselective hydroxylation of a 4- oxoproline enolate and the stereoselective reduction of the resulting ketoalcohol. An N-(9- phenylfluoren-9-yl) moiety is used not only as an N-protecting group but as a regio-and ...