Patent ID: 6509506
Filing Date: 2003-01-21
Classification: C07C

Abstract:
A method for converting an olefinic substrate to an asymmetric &agr;-amino aldehyde product, said asymmetric &agr;-amino aldehyde product being selected from a group consisting of deprotected asymmetric &agr;-amino aldehydes and a protected asymmetric &agr;-amino aldehyde intermediate having the protected amino radical, the method comprising the following steps:Step A: catalytically converting the olefinic substrate by a catalytic asymmetric aminohydroxylation reaction to a protected asymmetric &bgr;-aminohydroxide having a protected &bgr;-amino radical and a hydroxyl radical, said conversion employing a reaction solution which includes a source of the protected amino radical, an osmium compound as a catalyst, a chiral ligand for enantiomerically directing said catalytic asymmetric aminohydroxylation reaction, and a solvent; then Step B: optionally deprotecting the protected amino radical of the protected asymmetric &bgr;-aminohydroxide of said Step A to form a deprotected asymmetric &bgr;-aminohydroxide; Step C: oxidizing the hydroxyl radical on a first intermediate selected from the group consisting of the protected asymmetric &bgr;-aminohydroxide of said step A or the deprotected asymmetric &bgr;-aminohydroxide of said Step B to form the asymmetric &agr;-amino aldehyde product; and Step D: optionally deprotecting the protected amino radical of the protected asymmetric &bgr;-amino aldehyde intermediate of said Step C to form the deprotected asymmetric &agr;-amino aldehyde product.