Enantiopure 2-substituted glyceraldehyde derivatives by aza-Claisen rearrangement or C-alkylation of enamines

Katy L Bridgwood; C Christoph Tzschucke; Matthew O'Brien; Sven Wittrock; Jonathan M Goodman; John E Davies; Angus W J Logan; Matthias R M Hüttl; Steven V Ley

doi:10.1021/ol8018242

Enantiopure 2-substituted glyceraldehyde derivatives by aza-Claisen rearrangement or C-alkylation of enamines

Org Lett. 2008 Oct 16;10(20):4537-40. doi: 10.1021/ol8018242. Epub 2008 Sep 25.

Authors

Katy L Bridgwood¹, C Christoph Tzschucke, Matthew O'Brien, Sven Wittrock, Jonathan M Goodman, John E Davies, Angus W J Logan, Matthias R M Hüttl, Steven V Ley

Affiliation

¹ Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK.

PMID: 18816124
DOI: 10.1021/ol8018242

Abstract

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.