Synthesis of optically-active benzylic amines; asymmetric reduction of ketoxime ethers with chiral oxazaborolidines

…, E Roussey, S Tissandié, M Maftouh, P Roger

Index: Fontaine, Evelyne; Namane, Claudie; Meneyrol, Jerome; Geslin, Michel; Serva, Laurence; Roussey, Eliane; Tissandie, Stephanie; Maftouh, Mohamed; Roger, Pierre Tetrahedron Asymmetry, 2001 , vol. 12, # 15 p. 2185 - 2189

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Citation Number: 42

Abstract

The preparation of novel optically active benzylic amines by the enantioselective reduction of phenone oximes using chiral oxazaborolidine is described. The choice of the chiral 1, 2- amino alcohol (S)-diphenylvalinol as chiral inducer and that of the benzyl group for the O- oxime substituent is explained. 23 primary amines are obtained, with high enantioselectivity (ee= 98%), good yield (74%) on preparative scale. A mechanistic explanation is proposed.