Asymmetric enamide hydrogenation in the synthesis of N-acetylcolchinol: a key intermediate for ZD6126 |
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Authors: | Ian C Lennon Catherine J Brear James C Muir |
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Institution: | a Dowpharma, Chirotech Technology Ltd, A Subsidiary of The Dow Chemical Company, Unit 162, Cambridge Science Park, Milton Road, Cambridge, CB4 0GH, UK b Process R&D, AstraZeneca plc, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK |
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Abstract: | A synthesis of N-acetylcolchinol, a key intermediate in the synthesis of ZD6126, was developed. The enantiodifferentiating step required the catalytic asymmetric hydrogenation of an enamide. After screening a range of metal and ligand combinations it was found that (S,S)-iPr-FerroTANE Ru(methallyl)2 and (S,S)-tBuFerroTANE Rh(COD)]BF4 gave both high enantioselectivity (>90% ee) and high catalyst utility (molar S/C = 1000). |
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