Asymmetric Synthesis of α‑Arylcyclohexenones Catalyzed by Diphenylprolinol Silyl Ether

A general methodology for the asymmetric synthesis of α-arylcyclohexeneones from arylacetones and α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether followed by p-TSA-mediated cyclization is developed. A variety of arylacetones and α,β-unsaturated aldehydes were successfully convert...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-08, Vol.89 (15), p.10892-10902
Main Authors: Mehta, Ronak, Kumar, Rohtash, Singh, Suraj, Appayee, Chandrakumar
Format: Article
Language:English
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Summary:A general methodology for the asymmetric synthesis of α-arylcyclohexeneones from arylacetones and α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether followed by p-TSA-mediated cyclization is developed. A variety of arylacetones and α,β-unsaturated aldehydes were successfully converted to α-arylcyclohexeneones in 34–67% yield, 10:1–100:0 dr, and 81–99% ee. The scalability of this methodology by a gram-scale synthesis and their utility by converting the product to the corresponding epoxide, alcohol, and diol are demonstrated.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01234