Construction of Vicinal Quaternary Centers via Iridium-Catalyzed Asymmetric Allenylic Alkylation of Racemic Tertiary Alcohols
- Journal Article
Enantioselective bond formation between sterically hindered fragments to furnish acyclic products with vicinal quaternary centers is a formidable challenge. We report a solution that involves cocatalysis between a chiral Ir–(phosphoramidite,olefin) complex and La(OTf)3. This robust catalytic system effects highly enantioconvergent and regioselective alkylation of racemic tertiary α-allenyl alcohols with tetrasubstituted silyl ketene acetals. The transformation displays broad functional group tolerance for both reaction components and allows efficient generation of β-allenyl ester products in good yield and with excellent enantioselectivity. Furthermore, both the allene and ester functionalities were leveraged to upgrade the structural complexity of the products via a series of stereoselective metal-catalyzed functionalization reactions. Show more
Journal / seriesJournal of the American Chemical Society
Pages / Article No.
PublisherAmerican Chemical Society
Organisational unit03511 - Carreira, Erick M. / Carreira, Erick M.
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