Synthesis of C-2-symmetrical chiral aromatic diamines by diasteroselectiveaddition to bis(1,3-oxazolidinyl)aromatics with Grignard reagents

Ct-Symmetrical chiral bis(1,3-oxazolidinyl)aromatics were prepared by the c ondensation of aromatic dicarbaldehydes (p-benzene, m-benzene, 2,6-pyridine , 2,5-furan and 2,5-thiophene) with (R)-N-2,4, 6-trimethoxybenzyl phenylgly cinol (1). Bulky bis(1,3-oxazolidinyl)aromatics underwent diastereoselectiv e addition with Grignard reagents to give new classes of C-2- symmetrical c hiral diaminoaromatics in high yield and diastereoselectivity. The absolute configurations of bulky bis(1,3-oxazolidinyl)aromatics (3) and bis(tert-am ino)aromatics (10a) were confirmed by X-Ray spectroscopy.