Trichlorosilane-t-Amines

Thallium(III) trifluoroacetate, 295 Trichlorosilane-t-Amines, 322 Tris(tetrabutylammonium) pyrophosphate, 338 Amidation... 

Allylic phosphorus compounds Tris(tetrabutylammonium) pyrophosphate, 338 Allylsilanes t-Butyllithium, 58 Chlorotrimethylsilane-Lithium, 81 Lithium bis(dimethylphenylsilyl)-cuprate, 161 Methyllithium, 188 Trichlorosilane-t-Amines, 322 Allylic sulfur compounds (Phenylsulfonyl)allene, 247 Sodium benzenesulfinate, 289... 

Trichlorosilane (77 pL, 0.77 mmol) was added dropwise to a stirred solution of the imine (100 mg, 0.51 mmol) and catalyst (13.5 mg, 0.051 mmol) in anhydrous toluene (2 mL) at 0 °C, and the mixture was stirred at r.t. overnight under an argon atmosphere. The reaction was quenched with a saturated solution of NaHCC>3 (10 mL) and the product was extracted with ethyl acetate (3 x 30 mL). The extract was washed with brine, dried over anhydrous MgSC>4, and the solvent was evaporated. Purification using column chromatography on silica gel with a petroleum ether-ethyl acetate mixture (24 1) afforded the (S)-(+)-amine (81 mg, 81%, 92% ee) as an oil [a]D + 16.8 (c 0.5, MeOH). 

P. and Stoncius, S. (2010) Reduction of imines with trichlorosilane catalyzed by chiral Lewis bases, in Chiral Amine Synthesis (Methods, Developments and Applications) (ed. T. Nugent), John Wiley Sons, Ltd, Chichester, p. 131 ... 

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