Absolute stereochemistry assignment of N-phosphorylimine-derived aza-Diels-Alder adducts with TDDFF CD calculations

Di Bari, L.; Guillarme, S.; Hermitage, S.; Jay, D.A.; Pescitelli, G.; Whiting, A.

Abstract

N-Phosphorylimines undergo Lewis acid-catalyzed Diels-Alder reactions with Danishefsky's diene. Application of the chiral catalyst zinc (II)- (S)-BINOL results in good-to-low asymmetric induction but poor chemical conversion. However, the absolute stereochemistry of novel aza-Diels-Alder cycloadducts, such as diethyl 4-oxo-2-phenyl-3,4-dihydropyridin-1(2H)-ylphosphonate, can be determined using circular dichroism (CD). Comparison between experimental and TDDFT-calculated CD spectrum shows that use of the (S)-catalyst results in predominant formation of the (6R) cycloadducts. (c) 2005 Wiley-Liss, Inc.

Citation

Di Bari, L., Guillarme, S., Hermitage, S., Jay, D., Pescitelli, G., & Whiting, A. (2005). Absolute stereochemistry assignment of N-phosphorylimine-derived aza-Diels-Alder adducts with TDDFF CD calculations. Chirality, 17(6), 323-331

• Journal Article Type: Article
• Publication Date: 2005-06
• Journal: Chirality
• Print ISSN: 0899-0042
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 17
• Issue: 6
• Pages: 323-331