Amines to an end: Highly opticallyactive α‐CF3‐functionalized amines can be obtained using metal‐free reaction conditions. The method involves the transfer hydrogenation of CF3‐substituted ketimines catalyzed by 1 and reductive amination of CF3‐substituted ketones. The synthetic utility of this method was demonstrated by the synthesis of a CF3 analogue of NPS R‐568. PMP=para‐methoxyphenyl.
Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines
作者:Thomas Johnson、Mark Lautens
DOI:10.1021/ol401862g
日期:2013.8.16
[GRAPHICS]Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of alpha-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.