Organophotoredox/Ni-Cocatalyzed Allylation of Allenes: Regio- and Diastereoselective Access to Homoallylic Alcohols
Hui Xie, Bernhard Breit
Abstract
A dual organophotoredox/nickel-catalyzed reductive coupling of allenes with aldehydes has been developed for the rapid assembly of anti-homoallylic alcohols with high levels of regioselectivities (>20:1), diastereoselectivities (up to >20:1), and yields (up to 91%). The allylation was realized through a crucial π-allylnickel intermediate, which was obtained via insertion of allenes with a Ni–H intermediate. Moreover, γ,γ-disubstituted homoallylic alcohols with a quaternary stereocenter can also be prepared by this protocol.
Topics & Concepts
StereocenterChemistryCatalysisRegioselectivityNickelCombinatorial chemistryEnantioselective synthesisStereochemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions