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Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut–Currier reaction of allenoates

Author

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  • Weijun Yao

    (National University of Singapore)

  • Xiaowei Dou

    (National University of Singapore)

  • Shan Wen

    (National University of Singapore)

  • Ji’en Wu

    (National University of Singapore)

  • Jagadese J. Vittal

    (National University of Singapore)

  • Yixin Lu

    (National University of Singapore)

Abstract

The Rauhut–Currier (RC) reaction represents an efficient method for the construction of carbon–carbon bond in organic synthesis. However, the RC reactions involving allenoate substrates are very rare, and in particular, asymmetric intramolecular RC reaction of allenoates is yet to be discovered. Here, we show that the intramolecular RC reaction proceeds smoothly in the presence of 1 mol% β-ICD, and bicyclic lactones are obtained in high yields and with excellent enantiomeric excesses. With the employment of γ-substituted allenoates as racemic precursors, a novel dynamic kinetic resolution of allenes via RC reaction is observed, which allows for facile synthesis of highly enantiomerically enriched allenes.

Suggested Citation

  • Weijun Yao & Xiaowei Dou & Shan Wen & Ji’en Wu & Jagadese J. Vittal & Yixin Lu, 2016. "Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut–Currier reaction of allenoates," Nature Communications, Nature, vol. 7(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13024
    DOI: 10.1038/ncomms13024
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    Cited by:

    1. Sandip B. Jadhav & Soumya Ranjan Dash & Sundaram Maurya & Jagadeesh Babu Nanubolu & Kumar Vanka & Rambabu Chegondi, 2022. "Enantioselective Cu(I)-catalyzed borylative cyclization of enone-tethered cyclohexadienones and mechanistic insights," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

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