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Enantioselective synthesis of N,O-psiconucleosides

✍ Scribed by Ugo Chiacchio; Luisa Borrello; Daniela Iannazzo; Pedro Merino; Anna Piperno; Antonio Rescifina; Barbara Richichi; Giovanni Romeo

Book ID
104359998
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
175 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

The first enantioselective synthesis of b-D and b-L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1,3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyloxyacrylate followed by Vorbru Β¨ggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction.

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a β€œFull Text” option. The original article is trackable v