Asymmetric synthesis of (1R,1′R)- and (1S,1′S)-bis(1-arylethyl)amines by way of a diastereoselective addition to chiral imines and oxaxolidines with organometallic reagents
The asymmetric synthesis of the bis(α-methylbenzyl)amines, (1R,1′R)- and (1S,1′S)-bis(1-arylethyl)-amines 6, utilizing a diastereoselective reaction of chiral imines and oxazolidines derivedfrom (R)-phenylglycinol with Organometallic reagents, is described.
The reaction of MeLi or MeMgBr with chiral aromatic imines and 2-aryl-1,3-oxazolidines derived from (R)-phenylglycinol afforded with good diastereoselectivity (R,R,) -amines from imines, but the (R,S) -amines from 1,3-oxazolidines, respectively.