Iridium-Catalyzed C–C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation
There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.
Abstract
A chiral iridium complex formed in situ from [Ir(cod)Cl]2 and (R)-H8-BINAP is found
to catalyze the direct enantioselective C-C coupling of a simple propargyl ether,
TIPSOCH2C≡CH, with primary alcohols to form γ-hydroxy (Z)-enol silanes with uniformly
high enantioselectivity and complete alkene (Z)-stereoselectivity. As corroborated
by deuterium labeling studies, these studies represent the first examples of 1,2-hydride
shift-enabled π-allyl formation in the context of iridium catalysis.