Enantioselective Syntheses of Morpholines and Their Homologues via SN2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols
The Journal of Organic Chemistry2009Vol. 74(18), pp. 7013–7022
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Abstract
A highly regio- and stereoselective strategy for the syntheses in high yield and enantioselectivity of a variety of substituted nonracemic morpholines and their homologues is described. The reaction proceeds via an S(N)2-type ring opening of activated aziridines and azetidines by suitable halogenated alcohols in the presence of Lewis acid followed by base-mediated intramolecular ring closure of the resulting haloalkoxy amine.
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