145235-84-3Relevant articles and documents
Development of an asymmetric hydrogenation route to (S)- N -Boc-2,6-dimethyltyrosine
Praquin, Celine F. B.,De Koning, Pieter D.,Peach, Philip J.,Howard, Roger M.,Spencer, Sarah L.
experimental part, p. 1124 - 1129 (2012/01/06)
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 in catalyst loading.
A convenient asymmetric synthesis of the unnatural amino acid 2,6-dimethyl-L-tyrosine
Dygos,Yonan,Scaros,Goodmonson,Getman,Periana,Beck
, p. 741 - 743 (2007/10/02)
The title compound was prepared in high optical purity by a five-step synthesis from 3,5-dimethylphenol on a kilogram scale. The key steps were a modified palladium-catalyzed coupling of an aryl iodide with methyl 2-acetamidoacrylate and hydrogenation of the resulting sterically hindered dehydroamino acid 4 using [Rh(1,5-COD)(R,R-DIPAMP)]BF4 as catalyst.
