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Recent developments in the area of asymmetric transfer hydrogenation

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Wills, Martin, Palmer, Matthew, Smith, Athene, Kenny, Jennifer and Walsgrove, Tim. (2000) Recent developments in the area of asymmetric transfer hydrogenation. Molecules, Volume 5 (Number 1). pp. 4-18. ISSN 1420-3049

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Official URL: http://dx.doi.org/10.3390/50100004

Abstract

The use of an enantiomerically pure amino alcohol, coupled to a transfer hydrogenation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is described. 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 alpha-heteroatom substituted substrates, through the use of the appropriate protecting groups on each atom.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Hydrogenation, Amino alcohols, Ketones

Journal or Publication Title:

Molecules

Publisher:

M D P I AG

ISSN:

1420-3049

Official Date:

21 January 2000

Dates:

Date	Date Type
21 January 2000	Published
15 November 2000	Accepted
14 September 2000	Submitted

Volume:

Volume 5

Number:

Number 1

Number of Pages:

Page Range:

pp. 4-18

Identification Number:

10.3390/50100004

Status:

Peer Reviewed

Publication Status:

Published

Access rights to Published version:

Open Access

Funder:

Engineering and Physical Sciences Research Council (EPSRC), SmithKline Beecham, Oxford Asymmetry International plc

References:

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18, 187-208.
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York, 1993, Chapter 1.
6. Noyori, R. Organometallic ways for the multiplication of chirality. Tetrahedron 1994, 50, 4259-4292.
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John Wiley and Sons Ltd, 1997, pp 781-842.
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simple ketones catalyzed by Ruthenium(II) complexes. J. Org. Chem. 1996, 61, 4872-4873.
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13. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. Preferential hydrogenation of aldehydes and ketones. J. Am. Chem. Soc. 1995, 117, 10417-10418.
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ketones catalyzed by a Rh-PennPhos complex. Angew. Chem., Int. Edn. Engl. 1998, 37, 1100-
1103.
15. A summary of ligands (including our own) which have recently been reported for the asymmetric
transfer hydrogenation of ketones are given below. For reasons of space the comparison is limited
to the reduction of acetophenone.