An easy route to optically active 1-substituted-1-pyridyl-methylamines by diastereoselective reduction of enantiopure N-tert-butanesulfinyl ketimines

The reduction of enantiopure N-tert-butanesulfinyl ketimines derived from pyridyl ketones afforded the related N-tert-butanesulfinyl amines with high yields and diastereoselectivities.

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(RS)-N-[1-(Pyridin-2-yl)ethylidene]-2-methylpropane-2-sulfinamideC11H16N2OS[α]D25=-49.5 (c 0.075, CHCl3)Absolute configuration: (RS)

(RS)-N-[1-(Pyridin-3-yl)ethylidene]-2-methylpropane-2-sulfinamideC11H16N2OS[α]D25=+11.2 (c 0.040, CHCl3)Absolute configuration: (RS)

(RS)-N-[1-(Pyridin-4-yl)ethylidene]-2-methylpropane-2-sulfinamideC11H16N2OS[α]D25=-20.1 (c 0.141, CHCl3)Absolute configuration: (RS)

(RS)-N-[2-Methyl-1-(pyridin-2-yl)propylidene]-2-methylpropane-2-sulfinamideC13H20N2OS[α]D25=-171.0 (c 0.074, CHCl3)Absolute configuration: (RS)

(RS,S)-N-[1-(Pyridin-4-yl)ethyl]-2-methylpropane-2-sulfinamideC11H18N2OS[α]D25=-50.0 (c 0.036, CHCl3)Absolute configuration: (RS,S)Prepared from 4-acetylpyiridine

(RS)-N-[2,2-Dimethyl-1-(pyridin-2-yl)propylidene]-2-methylpropane-2-sulfinamideC14H22N2OS[α]D25=-179.7 (c 0.028, CHCl3)Absolute configuration: (RS)

(RS)-N-[Phenyl(pyridin-2-yl)methylene]-2-methylpropane-2-sulfinamideC16H18N2OS[α]D25=-123.6 (c 0.071, CHCl3)Absolute configuration: (RS)

(RS)-N-[Furan-2yl(pyridin-2-yl)methylene]-2-methylpropane-2-sulfinamideC14H16N2O2S[α]D25=-211.6 (c 0.029, CHCl3)Absolute configuration: (RS)

(RS)-N-[Pyridin-2-yl(thiophen-2-yl)methylene]-2-methylpropane-2-sulfinamideC14H16N2OS2[α]D25=-83.5 (c 0.074, CHCl3)Absolute configuration: (RS)

(RS,R)-N-[1-(Pyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamideC11H18N2OS[α]D25=-55.1 (c 0.092, CHCl3)Absolute configuration: (RS,R)Prepared from 2-acetylpyridine

(RS,S)-N-[1-(Pyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamideC11H18N2OS[α]D25=-41.3 (c 0.052, CHCl3)Absolute configuration: (RS,S)Prepared from 2-acetylpyridine

(RS,R)-N-[1-(Pyridin-3-yl)ethyl]-2-methylpropane-2- sulfinamideC11H18N2OS[α]D25=-33.2 (c 0.032, CHCl3)Absolute configuration: (RS,R)Prepared from 3-acetylpyridine

(RS,R)-N-[1-(Pyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamideC11H18N2OS[α]D25=-32.4 (c 0.094, CHCl3)Absolute configuration: (RS,R)Prepared from 4-acetylpyridine