Pd-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

Paul Knochel; Christoph Sämann

doi:10.1055/s-0033-1339973

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Synfacts 2013; 9(11): 1215
DOI: 10.1055/s-0033-1339973

Metal-Mediated Synthesis

Pd-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

Contributor(s):

Paul Knochel

,

Christoph Sämann

Johnson T, Lautens M * University of Toronto, Canada
Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines.

Org. Lett. 2013;
15: 4043-4045

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Further Information

Publication History

Publication Date:
18 October 2013 (online)

Abstract
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Key words

α-(trifluoromethyl)arylmethylamines - enantioselective synthesis - boronic acids - palladium

Significance

Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium catalysis to generate a variety of R-(trifluoromethyl)arylmethylamines with good to high enantioselectivity and yield.

Comment

The reported protocol is very versatile since it proceeds without the exclusion of ambient air and moisture. Moreover, several functional groups are tolerated, and readily available N,O-acetals synthesized from trifluoroaldehyde are used as starting materials.

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