Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to alpha-keto esters: synthesis of erythro beta-hydroxy dimethyl aspartates.
The photocycloaddition of methyl pyruvate and methyl phenylglyoxylate, respectively, to 5-methoxy oxazoles bearing additional substituents at C-2 and C-4 leads to bicyclic oxetanes 2 and 3 with high to moderate (exo) diastereoselectivity that can be easily ring-opened to give bis-quaternary aspartic acid diester derivatives 4 and 5.
Griesbeck
Axel G
AG
Institute of Organic Chemistry, University of Cologne, Greinstr. 4, D-50939 Köln, Germany. griesbeck@uni-koeln.de
Bondock
Samir
S
Lex
Johann
J