An Efficient Stereoselective Synthesis of <i>cis</i>-2,6-Disubstituted Tetrahydropyrans via Gold-Catalyzed Meyer–Schuster Rearrangement/Hydration/<i>oxa</i>-Michael Addition Sequence

Abstract

An efficient stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans 14a–c has been achieved via gold-catalyzed Meyer–Schuster rearrangement/hydration/oxa-Michael addition sequence from bis-propargylic alcohols 13a–c. The reaction of 13a proceeds via 2,6-disubstituted tetrahydropyran 14′a as an intermediate.

Keywords

• gold catalyst
• Meyer–Schuster rearrangement
• hydration
• <i>oxa</i>-Michael addition
• 2,6-disubstituted tetrahydropyrans