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.

Absolute Stereochemistry Assignment of N-Phosphorylimine-Derived Aza-Diels-Alder Adducts with TDDFT CD Calculations

DI BARI, LORENZO;PESCITELLI, GENNARO;
2005-01-01

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.
DI BARI, Lorenzo; Guillarme, S; Hermitage, S; Jay, Da; Pescitelli, Gennaro; Whiting, A.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/93424
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