Peptide-Catalyzed Kinetic Resolution of Formamides and Thioformamides as an Entry to Nonracemic Amines
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- 作者：Brandon S. Fowler ; Peter J. Mikochik ; Scott J. Miller
- 刊名：Journal of the American Chemical Society
- 出版年：2010
- 出版时间：March 10, 2010
- 年：2010
- 卷：132
- 期：9
- 页码：2870-2871
- 全文大小：158K
- 年卷期：v.132,no.9(March 10, 2010)
- ISSN：1520-5126
文摘
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 (krel) 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.