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Preparation of a chiral, nonracemic 2,5-diketopiperazine diene has enabled the investigation of intermolecular hetero-Diels-Alder cycloadditions. The diketopiperazine diene is reactive with both electron-rich and -deficient alkene substrates. Diastereofacial control in the cycloaddition is enforced with a removable aminal substituent. This study partly illuminates the regiochemical, stereoelectronic, and reactivity preferences of the diketopiperazine cycloaddition as well as provides a direct diastereoselective synthetic route to bicyclo[2.2.2]diazaoctane structures. © 2011 American Chemical Society


Erin N Morris, E Katherine Nenninger, Robert D Pike, Jonathan R Scheerer. Diels-Alder cycloaddition of chiral nonracemic 2,5-diketopiperazine dienes. Organic letters. 2011 Aug 19;13(16):4430-3

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PMID: 21770431

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