[2.2]-PARA-CYCLOPHANE-4-CARBALDEHYDE AS BUILDING-BLOCK FOR CHIRAL LIGANDS - PART II - EPOXIDATION OF ALKENES CATALYZED BY THE MN(III)-COMPLEX OF AN ATROPOISOMERICALLY PURE (ALPHA,BETA,ALPHA,BETA-TETRAARYLPORPHYRIN

The synthesis of the Mn(III)-complex of the new enantiopure, atropoiso merically pure chiral porphyrin (alpha,beta,alpha,beta)-1 is described . The compound was used as the catalyst in the epoxidation of unfuncti onalized olefins using aqueous NaOCl, 30%-H2O2 or PhIO as oxygen donor s. Up to 780 overall turnovers were obtained in the presence of NaOCl and PhIO, whereas with 30%-H2O2 only catalase activity was observed. C ontrary to expectations based on previous results [S. Banfi, A. Manfre di, F. Montanari, G. Pozzi, S. Quici, J. Mel. Catal., 113 (1996) 77], only racemic epoxides were obtained. (C) 1998 Elsevier Science B.V. Al l rights reserved.