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Construction of Vicinal Quaternary Centers via Iridium-Catalyzed Asymmetric Allenylic Alkylation of Racemic Tertiary Alcohols

Mayuko Isomura, David A. Petrone and Erick M. Carreira*

*ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, Email: erickm.carreiraorg.chem.ethz.ch

M. Isomura, D. A. Petrone, E. M. Carreira, J. Am. Chem. Soc., 2021, 143, 3323-3329.

DOI: 10.1021/jacs.1c00609


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Abstract

Cocatalysis between a chiral Ir-(phosphoramidite,olefin) complex and La(OTf)3 enables enantioselective bond formation between sterically hindered racemic tertiary α-allenyl alcohols and tetrasubstituted silyl ketene acetals to provide β-allenyl ester products in good yield and with excellent enantioselectivity.

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Key Words

allylation of esters


ID: J48-Y2021