Recent Developments in the Area of Asymmetric Transfer Hydrogenation 英文参考文献.docVIP

Molecules 2000, 5, 4-18 molecules ISSN 1420-3049 Recent Developments in the Area of Asymmetric Transfer Hydrogenation Martin Willsa,*, Matthew Palmera, Athene Smitha, Jennifer Kennya and Tim Walsgroveb aDepartment of Chemistry, University of Warwick, Coventry, CV4 7AL, UK Tel.: (024) 7652 3260, Fax: (024) 7652 4112, E-mail: M.Wills@warwick.ac.uk http://www.warwick.ac.uk/fac/sci/Chemistry/astaff/wills/ bSmithKline Beecham Pharmaceuticals, Old Powder Mills, Nr Leigh, Tonbridge, Kent, TN11 9AN, UK *Author to whom correspondence should be addressed. Received: 14 September 1999 / Accepted: 15 November 1999 / Published: 21 January 2000 Abstract: The use of an enantiomerically pure amino alcohol, coupled to a transfer hydro- genation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is de- scribed. The process works well for unfunctionalised ketones, affording e.e.s of up to 98%, and excellent conversions. We have recently extended, for the first time in this application, the scope of the methodology to the reductions of α-heteroatom substituted substrates, through the use of the appropriate protecting groups on each atom. Keywords: asymmetric, transfer, hydrogenation, catalysis, ruthenium. Introduction The asymmetric reduction of ketones to enantiomerically enriched alcohols remains a pivotal trans- formation in organic synthesis [1,2]. Of the methods available to achieve this reaction in a catalytic sense the most established are those based on either hydrogenation [3-7] or the use of oxazaboroli- dines for the catalysis of ketone reduction by borane [8,9]. Catalytic hydrogenation using a homochiral phosphine in conjunction with an appropriate metal, usually rhodium or ruthenium, is a versatile method which requires only very low levels of catalyst. In ? 2000 by MDPI (). Reproduction is permitted for noncommercial purposes.  5 Molecules 2000, 5 general, however, the method is most suita