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

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. Her...

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Published in:Nature communications 2016-10, Vol.7 (1), p.13024-13024, Article 13024
Main Authors: Yao, Weijun, Dou, Xiaowei, Wen, Shan, Wu, Ji’en, Vittal, Jagadese J., Lu, Yixin
Format: Article
Language:English
Subjects:
140/131
639/638/403/933
639/638/77/883
Catalysis
Humanities and Social Sciences
multidisciplinary
Science
Science (multidisciplinary)
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Summary: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. The Rauhut-Currier reaction is a powerful method to form carbon-carbon bonds. Here, the authors report an enantioselective intramolecular variant between alkenes and allenoates, giving access to highly functionalised bicyclic lactones in excellent enantiomeric excess.
ISSN:2041-1723
2041-1723
DOI:10.1038/ncomms13024