Abstract

A new annulation reaction leading to tetrahydropyrans has been discovered. The reaction of homoallylic enol ethers (e.g., 1) with alpha,beta-unsaturated ketones or esters begins with a Mukaiyama-Michael addition. The intermediate oxocarbenium ion undergoes a rapid 2-oxonia-Cope rearrangement, and the resulting zwitterion collapses to form a tetrahydropyran. The reaction is stereoselective with 3-butene-2-one, but leads to diastereomeric mixtures with ethyl acrylate. More complex enones, such as cyclohexenone, also undergo the reaction to produce fused ring products. The optical activity of the substrates is relayed in the tetrahydropyran products.

Full Text
Paper version not known

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.