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Diastereospecific Nazarov Cyclization of Fully Substituted Dienones: Generation of Vicinal All-Carbon-Atom Quaternary Stereocenters

Authors

  • Anais Jolit,

    1. Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA)
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  • Saleta Vazquez-Rodriguez,

    1. Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA)
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  • Dr. Glenn P. A. Yap,

    1. Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA)
    2. Department of Chemistry and Biochemistry, University of Delaware, 236 Brown Laboratory, Newark, DE 19716 (USA)
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  • Prof. Marcus A. Tius

    Corresponding author
    1. Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA)
    2. University of Hawaii Cancer Center, 701 Ilalo Street, Honolulu, HI 96813 (USA)
    • Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA)

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  • We thank the NIH-NIGMS (R01 GM57873) for partial support and the NSF for CRIF-MRI 1048367.

Abstract

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No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).

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