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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

Rezensent(en):
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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Publikationsverlauf

Publikationsdatum:
18. Oktober 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.


 

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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