L. Di Bari
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.
Authors
S. Guillarme
S. Hermitage
D.A. Jay
G. Pescitelli
Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor
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 |
Electronic ISSN | 1520-636X |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 17 |
Issue | 6 |
Pages | 323-331 |
Public URL | https://durham-repository.worktribe.com/output/1570619 |
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