Unprecedented catalytic asymmetric reduction of N-H imines.
Org Lett
; 7(2): 355-8, 2005 Jan 20.
Article
en En
| MEDLINE
| ID: mdl-15646996
ABSTRACT
[Reaction see text] Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.
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Banco de datos:
MEDLINE
Asunto principal:
Aminas
/
Hidrógeno
/
Iminas
/
Nitrógeno
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2005
Tipo del documento:
Article
País de afiliación:
Canadá