title: Absolute stereochemistry assignment of N-phosphorylimine-derived aza-Diels-Alder adducts with TDDFT CD calculations.
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.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Pisa, Italy.
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Di Bari
authors.forename: Stéphane
authors.initials: S
authors.lastname: Guillarme
authors.forename: Stephen
authors.initials: S
authors.lastname: Hermitage
authors.forename: David A
authors.initials: DA
authors.lastname: Jay
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
authors.forename: Andrew
authors.initials: A
authors.lastname: Whiting