Strong Enantioselective Self-Recognition of a Small Chiral Molecule

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• 作者：Seth E. Snyder ; Phillip I. Volkers ; David A. Engebretson ; Wonjae Lee ; William H. Pirkle ; James R. Carey
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：June 7, 2007
• 年：2007
• 卷：9
• 期：12
• 页码：2341 - 2343
• 全文大小：93K
• 年卷期：v.9,no.12(June 7, 2007)
• ISSN：1523-7052

文摘

In the present report, we have crystallized a single enantiomer and the racemate of N-3,5-dinitrobenzoyl (DNB) leucine. In both cases, theX-ray structures show clear evidence of homochiral dimerization in the solid state. Moreover, only homochiral dimers were observed in theunit cell of the racemate, a result of solid-state enantioselective complexation. The crystal structures support a chiral recognition mechanisminvolving two hydrogen bonds and an offset - interaction between the DNB rings.