Homologative Trifluoromethylation of Acetals

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

doi:10.1055/s-0033-1338485

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(13): 1857-1862
DOI: 10.1055/s-0033-1338485

paper

Homologative Trifluoromethylation of Acetals

James Y. Hamilton

,

Bill Morandi

,

Erick M. Carreira*

Abstract

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We dedicate this manuscript to Prof. Dr. Scott E. Denmark in honor of his 60^th birthday.

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.

Key words

antimony - acetals - insertion - diazo compounds - trifluoromethyl group

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Referenzen

References
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