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. 2011:7:997-1002.
doi: 10.3762/bjoc.7.112. Epub 2011 Jul 20.

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

Erwan Le Gall  1 , Antoine Pignon, Thierry Martens
Affiliations

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

Erwan Le Gall et al. Beilstein J Org Chem. 2011.

Abstract

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and the trapping of the acyliminium by an organozinc reagent. Most steps are conducted concomitantly to render the procedure as practical and straightforward as possible. Therefore, the whole experimental protocol takes less than two hours.

Keywords: acyliminium; amides; carbamates; multicomponent reactions; organozinc reagents.

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Figures

Scheme 1
Scheme 1
Addition of nucleophiles onto activated imines (A) or iminiums (B).
Scheme 2
Scheme 2
Activation of the aldimine with MsCl.
See this image and copyright information in PMC

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