Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation

C Bubert, J Blacker, S M Brown, J Crosby, S Fitzjohn, J P Muxworthy, T Thorpe, J M J Williams

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116 Citations (Scopus)

Abstract

Water-soluble analogues of Noyori's (1S,2S)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine and Knochel's (1R,2R)-N-(p-tolylsulfonyl)-1,2-diaminocyclohexane, containing an additional sulfonic acid group, have been synthesised. The ruthenium catalysed reduction of aromatic ketones using enantiomerically pure catalyst derived from water soluble ligands and [RuCl2(p-cymene)](2) has been examined. High enantioselectivity and moderate activity were observed in the 2-propanol/base system. The addition of water is necessary to stabilise the catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)4037-4039
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number24
Publication statusPublished - 2001

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