Catalytic asymmetric syntheses of tyrosine surrogates.

J Org Chem

Neuroscience Discovery Chemistry, Research & Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA.

Published: November 2008

Amino acid esters 5-11 as tyrosine mimics have been synthesized in excellent enantioselectivity (up to 99.6% ee) and in good overall chemical yields. The key step in the sequence was the Burk's [Rh(COD)(2R,5R)-Et-DuPhos]BF4-catalyzed asymmetric hydrogenation of enamides with a variety of reactive functional groups.

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http://dx.doi.org/10.1021/jo801577tDOI Listing

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