Optically pure fullerodendron formed by diastereoselective Diels–Alder reaction

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• 作者：Nobuhiro Takahashi ; Tomoyuki Tajima ; Naoki Tsugawa ; Yutaka Takaguchi
• 关键词：Fullerene ; Fullerodendron ; Diastereoselectivity ; Enantiomer ; Gluconamide
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：25 September 2010
• 年：2010
• 卷：66
• 期：39
• 页码：7787-7793
• 全文大小：670 K

文摘

The Diels–Alder reaction between C₆₀ and anthryl glycodendron, which has d- or l-gluconamides at the terminals, gave a new fullerene glycodendron conjugate. Interestingly, the diastereoselective cycloaddition reaction proceeded upon the treatment of C₆₀ with the anthryl dendron 3. Furthermore, optical pure fullerodendrons (−)-4L and (+)-4D, which were confirmed by ¹H and ¹³C NMR spectroscopy, FT-IR, MALDI-TOF mass spectroscopic analysis, were isolated from the mixture of diastereomers. And their absolute configurations were predicted by the use of CD spectra.