Homologative Trifluoromethylation of Acetals

Hamilton, James Y.; Morandi, Bill; Carreira, Erick M.

doi:10.1055/s-0033-1338485

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Homologative Trifluoromethylation of Acetals

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Morandi, Bill
Laboratorium für Organische Chemie, ETH Zürich, 8093 Zürich, Switzerland;
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Hamilton, J. Y., Morandi, B., & Carreira, E. M. (2013). Homologative Trifluoromethylation of Acetals. Synthesis, 45(13), 1857-1862. doi:10.1055/s-0033-1338485.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-BBC2-E

Abstract

Trifluoroethyl α-insertion of acetals has been developed. Aromatic, heteroaromatic, and alkenyl acetals react with in situ generated (trifluoromethyl)diazomethane in the presence of antimony(V) chloride to furnish α-trifluoromethyl acetals. A stereoselective version of this transformation exploiting the acetal as a chiral auxiliary is also presented.