Synthesis of trans-epoxy-l-proline and cis-aziridino-l-proline from S-pyroglutamic acid. Regio-and diastereoselective ring opening of its derivatives

…, A Aschenbrenner, A Kirfel, F Schwabenländer

Index: Herdeis, Claus; Aschenbrenner, Andrea; Kirfel, Armin; Schwabenlaender, Franz Tetrahedron Asymmetry, 1997 , vol. 8, # 14 p. 2421 - 2432

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Citation Number: 37

Abstract

The pyroglutamic acid derivative 4 was converted through several steps into 2S, 3R, 4S- epoxyproline 8. Key steps of the reaction sequence were the stereoselective epoxidation of 4 to 5 and the chemoselective reduction of the amide group of 5 with concomitant transformation of the acetal moiety into the N-benzyl protecting group without oxirane ring opening. The air sensitive benzyl derivative was transformed to the stable N-Boc prolinol ...