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Issue 8, 2004
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Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to α-keto esters: synthesis of erythro β-hydroxy dimethyl aspartates

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Abstract

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.

Graphical abstract: Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to α-keto esters: synthesis of erythro β-hydroxy dimethyl aspartates

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Publication details

The article was received on 10 Feb 2004, accepted on 01 Mar 2004 and first published on 17 Mar 2004


Article type: Communication
DOI: 10.1039/B401990C
Citation: Org. Biomol. Chem., 2004,2, 1113-1115
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    Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to α-keto esters: synthesis of erythro β-hydroxy dimethyl aspartates

    A. G. Griesbeck, S. Bondock and J. Lex, Org. Biomol. Chem., 2004, 2, 1113
    DOI: 10.1039/B401990C

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