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Reversal Diastereoselectivity Between the Organomagnesium and Organolithium Reagents on Chiral N-Tert-Butylsulfinylaldimines for the Preparation of Chiral Amines |
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| Authors: | Chinnapillai Rajendiran Periyandi Nagarajan A Naidu P K Dubey |
| Institution: | 1. Suven Life Sciences Ltd., Research and Development Center , Hyderabad , India;2. Department of Chemistry , J.N.T. University , Hyderabad , India |
| Abstract: | The asymmetric synthesis of both the enantiomer of chiral amines from the single chiral source of N-tert-butylsulfinylaldimines (3) by simply changing the organometallic reagents through diastereoselective addition. An efficient enantioselective synthesis of chiral amines including (S)-3-methyl-1-(2-piperidin-1-yl-phenyl)butyl amine (6a), a key intermediate to prepare antidiabetic drug repaglinide (1), is reported. |
| Keywords: | 1-(2-Bromophenyl)piperidine isobutyraldehyde isovaleraldehyde n-butyraldehyde n-propionaldehyde S(–)-tert-butanesulfinamide titanium tetraethoxide |