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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	Event
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

Identifier:

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:

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons Ltd: NY, 1994.
2. Ojima, I. Catalytic Asymmetric Synthesis; VCH Press: Berlin, 1993.
3. Noyori, R. Chemical multiplication of chirality - science and applications. Chem. Soc. Rev. 1989,
18, 187-208.
4. Noyori, R.; Takaya, H. BINAP - An efficient chiral element for asymmetric catalysis. Acc. Chem.
Res. 1990, 23, 345-350.
5. Takaya, H.; Ohno, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New
York, 1993, Chapter 1.
6. Noyori, R. Organometallic ways for the multiplication of chirality. Tetrahedron 1994, 50, 4259-4292.
7. Wills, M. in Supplement A3: The chemistry of double-bonded functional groups; Patai, S., Ed.;
John Wiley and Sons Ltd, 1997, pp 781-842.
8. Deloux, L.; Srebnik, M. Asymmetric boron-catalyzed reactions. Chem. Rev. 1993, 93, 763-784.
9. Wallbaum, S.; Martens, J. Asymmetric syntheses with chiral oxazaborolidines. Tetrahedron
Asymmetry 1992, 3, 1475-1504.
10. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Practical enantioselective hydrogenation of aromatic ketones. J. Am. Chem. Soc. 1995, 117, 2675-2676.
11. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. Stereoselective hydrogenation of
simple ketones catalyzed by Ruthenium(II) complexes. J. Org. Chem. 1996, 61, 4872-4873.
12. Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Asymmetric hydrogenation of cyclic alpha,beta-unsaturated ketones to chiral allylic alcohols. Synlett 1997, 467-469.
13. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. Preferential hydrogenation of aldehydes and ketones. J. Am. Chem. Soc. 1995, 117, 10417-10418.
14. Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Highly enantioselective hydrogenation of simple
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.