Abstract
Stereoselective construction of multi-substituted tetrahydrofurans is described. The procedure is consisted in three steps: stereoselective Michael/aldol tandem reaction, alkenylation, and radical cyclization. A chiral or racemic adduct of the tandem Michael/aldol reaction, β-hydroxyl-α-(phenylseleno)alkyl carbonyl compound, was alkenylated by treatment with propiolic ester to give a precursor of radical cyclization in good yields. Exposure of the precursor to Bu 3SnH in hot toluene gave tri- or tetrasubstituted tetrahydrofurans in a good yield. The good control of relative configuration between C2 and C3 during the tandem reaction stage and the excellent 2,5- cis-induction in the radical cyclization brought the stereoselective formation of trisubstituted tetrahydrofurans. A prochiral radical carbon generated from a secondary selenide attacked the double bond in a stereoselective manner and one of four possible diastereomers of tetrahydrofuran was formed stereoselectively.
Sign-in/Register to access full text options 
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 callDisclaimer: 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.
