Chiral Recognition and Kinetic Resolution of Aromatic Amines via Supramolecular Chiral Nanocapsules in Nonpolar Solvents

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• 作者：Toshiyuki Kida ; Takuya Iwamoto ; Haruyasu Asahara ; Tomoaki Hinoue ; Mitsuru Akashi
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：March 6, 2013
• 年：2013
• 卷：135
• 期：9
• 页码：3371-3374
• 全文大小：246K
• 年卷期：v.135,no.9(March 6, 2013)
• ISSN：1520-5126

文摘

Herein we report the first example of chiral recognition and kinetic resolution of aromatic amine guests using supramolecular nanocapsules assembled from cyclodextrin derivatives in nonpolar media. With these nanocapsules, an extremely high chiral recognition of 1-(1-naphthyl)ethylamine (1) in cyclohexane was achieved, with a binding selectivity of up to 41 for (S)-1 over (R)-1. In addition, kinetic resolution of 1 through enantioselective N-acylation was accomplished with an enantiomeric excess of up to 91%.