Asymmetric Hydrogenation of N-Sulfonylated--dehydroamino Acids: Toward the Synthesis of an Anthrax Lethal Factor Inhibitor

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• 作者：C. Scott Shultz ; Spencer D. Dreher ; Norihiro Ikemoto ; J. Michael Williams ; Edward J. J. Grabowski ; Shane W. Krska ; Yongkui Sun ; Peter G. Dormer ; and Lisa DiMichele
• 刊名：Organic Letters
• 出版年：2005
• 出版时间：August 4, 2005
• 年：2005
• 卷：7
• 期：16
• 页码：3405 - 3408
• 全文大小：80K
• 年卷期：v.7,no.16(August 4, 2005)
• ISSN：1523-7052

文摘

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A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated--dehydroamino acids has been discovered and demonstratedin 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, andthis work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

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