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Diastereoselective Synthesis of 2,6-Disubstituted Tetrahydropyranones via Prins Cyclization of 3-Bromobut-3-en-1-ols and Aldehydes

Surjya Kumar Bora, Sudip Shit, Archana Kumari Sahu and Anil K. Saikia*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India, Email: asaikiaiitg.ac.in

S. K. Bora, S. Shit, A. K. Sahu, A. K. Saikia, J. Org. Chem., 2023, 88, 3012-3021.

DOI: 10.1021/acs.joc.2c02715


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Abstract

Tetrahydropyranones are synthesized from 3-bromobut-3-en-1-ols and aldehydes in good yields with excellent diastereoselectivity at -35 C. The carbonyl moiety can be used for Wittig reaction, cis-selective reduction with lithium aluminum hydride, and for the synthesis of aminoguanidine compounds.


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proposed mechanism



Key Words

O-heteroycles, Prins Reaction


ID: J42-Y2023