Stereoselective Syntheses of Highly Substituted Tetrahydrofurans based on Matteson Homologations.

Chemistry

Organic Chemistry I, Saarland University, Campus C4.2, D-, 66123, Saarbrücken.

Published: March 2025

Deprotonated trimethylsilylethanol is an excellent nucleophile for Matteson homologations. It can be introduced in high yields and the products are stable under the usual basic reaction conditions. After two further homologation steps, the protective group is automatically cleaved off via a six-membered ring O-B coordination, providing highly substituted tetrahydrofurans.

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http://dx.doi.org/10.1002/chem.202500560DOI Listing

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