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Issue 22, 2006
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N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels–Alder cycloadditions of 9-substituted anthracene derivatives

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Abstract

Chiral 9-oxazolidinyl anthracene derivatives have been prepared as single diastereoisomers by condensation of 9-anthraldehyde with the appropriate N-alkyl amino alcohol. Asymmetric Diels–Alder cycloadditions of these with N-methyl maleimide proceeds in good yield and in good diastereoselectivity, the sense of which may be controlled by judicious choice of the N-alkyl group.

Graphical abstract: N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels–Alder cycloadditions of 9-substituted anthracene derivatives

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Publication details

The article was received on 13 Jul 2006, accepted on 15 Sep 2006 and first published on 02 Oct 2006


Article type: Paper
DOI: 10.1039/B610055D
Citation: Org. Biomol. Chem., 2006,4, 4206-4213
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    N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels–Alder cycloadditions of 9-substituted anthracene derivatives

    H. Adams, R. A. Bawa and S. Jones, Org. Biomol. Chem., 2006, 4, 4206
    DOI: 10.1039/B610055D

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