Base-Catalyzed Traceless Silylation and Deoxygenative Cyclization of Chalcones to Cyclopropanes

Development of simple synthetic methods from readily available compounds to complex products is of utmost interest in modern synthesis. Catalytic synthesis of cyclopropanes is important for diverse chemical applications. We present a method for the transformation of readily accessible α,β-unsaturate...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-05, Vol.87 (10), p.6695-6709
Main Authors: Sahu, Manas Kumar, Jaiswal, Shubham, Pattanaik, Sandip, Gunanathan, Chidambaram
Format: Article
Language:English
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Summary:Development of simple synthetic methods from readily available compounds to complex products is of utmost interest in modern synthesis. Catalytic synthesis of cyclopropanes is important for diverse chemical applications. We present a method for the transformation of readily accessible α,β-unsaturated ketones (chalcones) to cyclopropanes. A simple base, KOH, catalyzed the selective reduction of the enone carbonyl functionality, dehydrogenative silylation, and deoxygenative cyclization of chalcones to provide the cyclopropane products. Chalcones with extended conjugation and 4-chromanone-based substrates also provided the corresponding cyclopropanes. One-pot synthesis of cyclopropanes directly from industrial feedstock compounds such as ketones and aldehydes is also demonstrated using catalytic KOH for both intermolecular condensation and dehydrogenative silylation-deoxygenative intramolecular cyclization cascade.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00374