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J Org Chem. 2011 Jul 1;76(13):5461-5. doi: 10.1021/jo200548g. Epub 2011 Jun 7.

Chromium-mediated stereoselective synthesis of carbohydrate-derived (E)-α,β-unsaturated esters or amides.

Author information

1
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain.

Abstract

A chromium-mediated novel synthesis of carbohydrate-derived di- and trisubstituted (E)-α,β-unsaturated esters or amides from a range of dichloroesters or amides and a variety of sugar aldehydes is reported. The process took place with total stereoselectivity and in high yields. A mechanism based on a sequential chromium-promoted aldol-type reaction and a completely stereoselective β-elimination reaction is proposed to explain these results.

PMID:
21612264
DOI:
10.1021/jo200548g
[Indexed for MEDLINE]

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