Tetrahedron

Asymmetric syntheses via metalated chiral hydrazones: overall enantioselective α-alkylation of acyclic ketones

…, H Eichenauer, U Baus, H Schubert, KAM Kremer

Index: Enders, D.; Eichenauer, H.; Baus, U.; Schubert, H.; Kremer, K. A. M. Tetrahedron, 1984 , vol. 40, # 8 p. 1345 - 1359

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Citation Number: 104

Abstract

A general method is described, which allows the overall enantioselective α-alkylation of acyclic ketones in good overall yields (44–86%,, 4 steps) and enantioselectivities ranging routinely from> 94% ee up to virtually complete asymmetric induction (99.5% ee). The acyclic ketones are transformed to their corresponding “SAMP-hydrazones”(S)-2 by reaction with the enantiomerically pure hydrazine (S)-l-amino-2-methoxymethyl-pyrrolidine [SAMP, ...