Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones

We report a catalytic asymmetric Nazarov cyclization of simple, acylic, alkyl-substituted divinyl ketones using our recently disclosed strong and confined imidodiphosphorimidate Brønsted acids. The corresponding monocyclic cyclopentenones are formed in good yields and excellent regio-, diastereo-, a...

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Veröffentlicht in:Journal of the American Chemical Society 2019-02, Vol.141 (8), p.3414-3418
Hauptverfasser: Ouyang, Jie, Kennemur, Jennifer L, De, Chandra Kanta, Farès, Christophe, List, Benjamin
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Sprache:eng
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Zusammenfassung:We report a catalytic asymmetric Nazarov cyclization of simple, acylic, alkyl-substituted divinyl ketones using our recently disclosed strong and confined imidodiphosphorimidate Brønsted acids. The corresponding monocyclic cyclopentenones are formed in good yields and excellent regio-, diastereo-, and enantioselectivities. Further, the chemical utility of the obtained enantiopure cyclopentenones is demonstrated.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b13899