Epoxy Aldehyde (epoxy + aldehyde)

Distribution by Scientific Domains


Selected Abstracts


ChemInform Abstract: Metal-Mediated Diastereoselective Allylation Reaction of Chiral ,,,-Epoxy Aldehyde.

CHEMINFORM, Issue 6 2009
Part 2.
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


Direct Access to Furanosidic Eight-Membered Ulosonic Esters from cis -,,,-Epoxy Aldehydes

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 4 2003
Claudia H. Sugisaki
Abstract Direct access to bicyclic precursors of octulosonic acids is achieved by treatment of differentially (or not) protected ,,,-bis(silyloxy) cis -,,,-epoxy aldehydes with ethyl 2-(trimethylsilyloxy)-2-propenoate in the presence of boron trifluoride,diethyl ether. An X-ray crystallographic structure of a bicycle (compound 33a) was obtained and used to determine the absolute configurations of the different stereogenic centers and thus the diastereoselective preference of the aldol reaction (syn) and the regioselectivity of the epoxide ring-opening (C-6 atom). Functionalization and opening of the bicyclic compound to afford octulosonic analogues in their furanoside forms was studied. An octulosonic 8-phosphate analogue has been synthesized. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]


A Flexible Route Towards Five-Membered Ring Imino Sugars and Their Novel 2-Deoxy-2-fluoro Analogues

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 15 2003
Tahar Ayad
Abstract A flexible route towards five-membered ring imino sugars starting from a chiral ,,,-epoxy aldehyde has been developed. The approach relies on the use of the versatile epoxyamine intermediate 4, from which regiocontrolled epoxide opening affords diastereoselective access to trisubstituted pyrrolidines. Described here is the nucleophilic attack at C-2 of the pivotal epoxypyrrolidine 10, leading to the biologically relevant imino sugars 1,4-dideoxy-1,4-imino- D -arabinitol (2) and 1,4-dideoxy-1,4-imino- L -galactitol (3) as well as their novel 2-deoxy-2-fluoro analogues, after oxidative manipulation of the vinyl moiety. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]


Direct Access to Furanosidic Eight-Membered Ulosonic Esters from cis -,,,-Epoxy Aldehydes

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 4 2003
Claudia H. Sugisaki
Abstract Direct access to bicyclic precursors of octulosonic acids is achieved by treatment of differentially (or not) protected ,,,-bis(silyloxy) cis -,,,-epoxy aldehydes with ethyl 2-(trimethylsilyloxy)-2-propenoate in the presence of boron trifluoride,diethyl ether. An X-ray crystallographic structure of a bicycle (compound 33a) was obtained and used to determine the absolute configurations of the different stereogenic centers and thus the diastereoselective preference of the aldol reaction (syn) and the regioselectivity of the epoxide ring-opening (C-6 atom). Functionalization and opening of the bicyclic compound to afford octulosonic analogues in their furanoside forms was studied. An octulosonic 8-phosphate analogue has been synthesized. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]