D-Allal- and D-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles

The regioselectivity and stereoselectivity were examined of the addition reactions of O-, C-, N-and S-nucleophiles to D-allal- and D-galactal-derived N-mesylaziridines. The ratio of 1,4-regioselectivity (exclusive syn-1,4-addition) to 1,2-regioselectivity (exclusive anti-1,2-addition) was strictly a...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 18; pp. 2863 - 2871
Main Authors Di Bussolo, Valeria, Frau, Ileana, Pineschi, Mauro, Crotti, Paolo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.09.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
regioselectivity
stereoselectivity
heterocycles
STRATEGY
OXIRANE
nucleophilic additions
GLYCOSYLATION
SUGARS
AZIDE
GLYCOSIDATION
glycosylations
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Summary:The regioselectivity and stereoselectivity were examined of the addition reactions of O-, C-, N-and S-nucleophiles to D-allal- and D-galactal-derived N-mesylaziridines. The ratio of 1,4-regioselectivity (exclusive syn-1,4-addition) to 1,2-regioselectivity (exclusive anti-1,2-addition) was strictly and directly dependent on the ability of the nucleophile to coordinate with the nitrogen atom of the aziridine.
ISSN:0039-7881
DOI:10.1055/s-0031-1291137