Diels-Alder cycloaddition of chiral nonracemic 2,5-diketopiperazine dienes.

  title={Diels-Alder cycloaddition of chiral nonracemic 2,5-diketopiperazine dienes.},
  author={Erin N Morris and E Katherine Nenninger and Robert D Pike and Jonathan R Scheerer},
  journal={Organic letters},
  volume={13 16},
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… CONTINUE READING