Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2, 6-dimethyltyrosine

CFB Praquin, PD de Koning, PJ Peach…

Index: Praquin, Celine F. B.; De Koning, Pieter D.; Peach, Philip J.; Howard, Roger M.; Spencer, Sarah L. Organic Process Research and Development, 2011 , vol. 15, # 5 p. 1124 - 1129

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Citation Number: 15

Abstract

An improved, simpler and potentially more economical route to (S)-N-Boc-2, 6- dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3, 5-dimethylphenyl acetate 4 and to identify a significantly more active asymmetric hydrogenation catalyst that allowed a 5-fold reduction ...