Catalyst‐Directed Diastereo‐ and Site‐Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3‐Diols: Protecting‐Group‐Free Synthesis of Substituted Pyrans

Abstract

The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.