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EPSRC Reference: GR/N31429/02
Title: PRACTICAL ASYMMETRIC SYNTHESIS OF POLYFUNCTIONAL DISUBSTITUTED AMINO ACIDS
Principal Investigator: Marsden, Professor SP
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Sch of Chemistry
Organisation: University of Leeds
Scheme: Standard Research (Pre-FEC)
Starts: 01 August 2001 Ends: 31 January 2004 Value (£): 38,427
EPSRC Research Topic Classifications:
Asymmetric Chemistry
EPSRC Industrial Sector Classifications:
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Summary on Grant Application Form
The programme aims to develop general and practical methods for the asymmetric synthesis of alpha,alpha-disubstituted amino acids of medicinal importance. The key step in the synthesis is an asymmetric deconjugative alkylation/amination of an unsaturated pseudoephedrine amide. The precursors for this key step are readily prepared by condensation of shelf-stable pseudoephedrine containing phosphonates or active methylene compounds with aldehydes, thus allowing the synthesis of diverse precursors from the vast array of commercially available aldehydes. The reaction not only forms an asymmetric quarternary centre, but also allows the stereocontrolled introduction of an olefin which can be used as a point of introduction of further functionality. This is exemplified by the shortest asymmetric synthesis to date of the important immunosuppressive agent myriocin.
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Organisation Website: http://www.leeds.ac.uk