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. 2005 Aug 4;7(16):3405-8.
doi: 10.1021/ol050869s.

Asymmetric hydrogenation of N-sulfonylated-alpha-dehydroamino acids: toward the synthesis of an anthrax lethal factor inhibitor

C Scott Shultz  1 , Spencer D Dreher, Norihiro Ikemoto, J Michael Williams, Edward J J Grabowski, Shane W Krska, Yongkui Sun, Peter G Dormer, Lisa Dimichele
Affiliations

Asymmetric hydrogenation of N-sulfonylated-alpha-dehydroamino acids: toward the synthesis of an anthrax lethal factor inhibitor

C Scott Shultz et al. Org Lett. .

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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