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Synfacts 2013; 9(11): 1215
DOI: 10.1055/s-0033-1339973
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

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)

 
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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.


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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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