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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

123 Citations (SciVal)

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 language	English
Pages (from-to)	4037-4039
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	24
Publication status	Published - 2001

Cite this

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title = "Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation",

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.",

author = "C Bubert and J Blacker and Brown, {S M} and J Crosby and S Fitzjohn and Muxworthy, {J P} and T Thorpe and Williams, {J M J}",

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year = "2001",

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volume = "42",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation

AU - Bubert, C

AU - Blacker, J

AU - Brown, S M

AU - Crosby, J

AU - Fitzjohn, S

AU - Muxworthy, J P

AU - Thorpe, T

AU - Williams, J M J

N1 - ID number: ISI:000169116400020

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

M3 - Article

SN - 0040-4039

VL - 42

SP - 4037

EP - 4039

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

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

Abstract

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