title: Diels-Alder cycloaddition of chiral nonracemic 2,5-diketopiperazine dienes.
abstract: 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.
authors.affiliation: Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, USA.
authors.forename: Erin N
authors.initials: EN
authors.lastname: Morris
authors.forename: E Katherine
authors.initials: EK
authors.lastname: Nenninger
authors.forename: Robert D
authors.initials: RD
authors.lastname: Pike
authors.forename: Jonathan R
authors.initials: JR
authors.lastname: Scheerer
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D007212:Indolizines; D007659:Ketones; D010879:Piperazines; D013141:Spiro Compounds; C084043:VM 55599