Tetrahedron letters

Enantiomerically pure 2-piperazinemethanols as novel chiral ligands of oxazaborolidine catalysts in enantioselective borane reductions

T Inoue, D Sato, K Komura, S Itsuno

Index: Inoue, Tsutomu; Sato, Daisuke; Komura, Kenichi; Itsuno, Shinichi Tetrahedron Letters, 1999 , vol. 40, # 29 p. 5379 - 5382

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Citation Number: 26

Abstract

ABSTRACT: Novel enantiomerically pure 2-piperazinemethanols (3–5) were synthesized from 2-piperazinecar☐ ylic acid 1. The asymmetric reduction of aromatic ketones, ketimine and oxime ether has been performed with reagents prepared from 2-piprazinemethanol and borane to yield enantiomerically enriched alcohols and amines, respectively. The preferred absolute configuration of the product was dependent on the structure of the sulfonyl ...