Peptide-Catalyzed Kinetic Resolution of Formamides and Thioformamides as an Entry to Nonracemic Amines

We report a fundamentally unique approach to the catalytic kinetic resolution of amine derivatives based on formamide and thioformamide substrates. Readily accessible histidine-containing peptides mediate the kinetic resolutions with as little as 5 mol % catalyst. Selectivity factors (k rel) as high...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 9; pp. 2870 - 2871
Main Authors Fowler, Brandon S, Mikochik, Peter J, Miller, Scott J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.03.2010
Amer Chemical Soc
Subjects
Amines - chemistry
Carbonates - chemical synthesis
Carbonates - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Kinetics
Peptides - chemistry
Physical Sciences
Science & Technology
ACYLATION
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Summary:We report a fundamentally unique approach to the catalytic kinetic resolution of amine derivatives based on formamide and thioformamide substrates. Readily accessible histidine-containing peptides mediate the kinetic resolutions with as little as 5 mol % catalyst. Selectivity factors (k rel) as high as 43.7 were observed under simple reaction conditions utilizing Boc2O as the reagent at room temperature. Mechanistic experiments were conducted that established a higher level of reactivity for thioformamide substrates than for their formamide analogues. The products of these asymmetric reactions were shown to be readily converted to desirable building blocks such as N-Boc-amines and the parent chiral formamide compounds.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja9107897