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

Abstract

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.

Key words

glycosylations - regioselectivity - stereoselectivity - nucleophilic additions - heterocycles

• References

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