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

Weijun Yao, Xiaowei Dou, Shan Wen, Ji’en Wu, Jagadese J. Vittal and Yixin Lu ()
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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

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms13024

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