Asymmetric Hydrogenation of N-Sulfonylated-α-dehydroamino Acids: Toward the Synthesis of an Anthrax Lethal Factor Inhibitor
Organic Letters2005Vol. 7(16), pp. 3405–3408
Citations Over TimeTop 16% of 2005 papers
C. Scott Shultz, Spencer D. Dreher, Norihiro Ikemoto, J. Michael Williams, Edward J. J. Grabowski, Shane W. Krska, Yongkui Sun, Peter G. Dormer, Lisa DiMichele
Abstract
A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-alpha-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst. [reaction: see text]
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