Stereodivergent Synthesis of d,d- and l,l-glycero-β-allo-Heptopyranoses on a Dioxanone Scaffold

Nagarjuna Palyam; Izabella Niewczas; Marek Majewski

doi:10.1055/s-0032-1290461

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(16): 2367-2370
DOI: 10.1055/s-0032-1290461

letter

Stereodivergent Synthesis of d,d- and l,l-glycero-β-allo-Heptopyranoses on a Dioxanone Scaffold

Authors

Nagarjuna Palyam

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada, Fax: +1(306)9664730 eMail: marek.majewski@usask.ca
Izabella Niewczas

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada, Fax: +1(306)9664730 eMail: marek.majewski@usask.ca
Marek Majewski*

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada, Fax: +1(306)9664730 eMail: marek.majewski@usask.ca

Abstract

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Abstract

We report a stereodivergent synthesis of both enantiomers of glycero-allo-heptose from 2,2-dimethyl-1,3-dioxan-5-one, a readily available nonchiral scaffold, and from two different synthetic equivalents of glyoxal: dimethoxyacetaldehyde and 1,3-dithiane-2-carboxaldehyde. The short synthetic sequence involves first a proline-mediated, and then a lithium enolate mediated aldol reaction at the α- and α′-positions of the dioxanone ring, respectively, and demonstrates the complementary nature of organocatalysis and metal enolate based methods.

Key words

aldol reaction - organocatalysis - carbohydrates - heterocycles - stereoselective synthesis

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Referenzen

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