Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid

Di Bari, L.; Guillarme, S.; Hermitage, S.; Howard, J.A.K.; Jay, D.A.; Pescitelli, G.; Whiting, A.; Yufit, D.S.

Abstract

N-Phosphoryl imines react with oxygenated dienes in the presence of Lewis acids to provide either the formal aza-Diels-Alder adduct, or the acyclic Mannich-type addition product, depending upon the catalyst and work up used, which is in agreement with the hypothesis that these reactions are mediated by zwitterionic Lewis acid-complex intermediates, rather than a concerted cyclo-addition transition-state followed by hydrolytic ring opening. Stoichiometric asymmetric induction can be achieved using a zinc(II)binol complex, producing up 77% ee.

Citation

Di Bari, L., Guillarme, S., Hermitage, S., Howard, J., Jay, D., Pescitelli, G., Whiting, A., & Yufit, D. (online). Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 708-710

• Journal Article Type: Article
• Journal: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
• Print ISSN: 0936-5214
• Electronic ISSN: 1437-2096
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Issue: 4
• Pages: 708-710
• Public URL: https://durham-repository.worktribe.com/output/1602852