Enantiopure 2-Substituted Glyceraldehyde Derivatives by Aza-Claisen Rearrangement or C-Alkylation of Enamines

Enantiopure 2-Substituted Glyceraldehyde Derivatives by Aza-Claisen Rearrangement or C-Alkylation of Enamines

2-Alkyl derivatives of butane-2,3-diacetal (BDA) protected glyceraldehyde were stereoselectively prepared by aza-Claisen rearrangement of N-allyl-enammonium ions or C-alkylation of enamines. This allows rapid and convenient access to densely functionalized chiral building blocks.

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Veröffentlicht in:Organic letters 2008-10, Vol.10 (20), p.4537-4540
Hauptverfasser: Bridgwood, Katy L, Tzschucke, C. Christoph, O’Brien, Matthew, Wittrock, Sven, Goodman, Jonathan M, Davies, John E, Logan, Angus W. J, Hüttl, Matthias R. M, Ley, Steven V
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Sprache:eng
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Zusammenfassung:2-Alkyl derivatives of butane-2,3-diacetal (BDA) protected glyceraldehyde were stereoselectively prepared by aza-Claisen rearrangement of N-allyl-enammonium ions or C-alkylation of enamines. This allows rapid and convenient access to densely functionalized chiral building blocks.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8018242