Enantioselective Syntheses of Morpholines and Their Homologues via SN2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols

Ghorai, Manas K. ; Shukla, Dipti ; Das, Kalpataru (2009) Enantioselective Syntheses of Morpholines and Their Homologues via SN2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols The Journal of Organic Chemistry, 74 (18). pp. 7013-7022. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo901297d

Related URL: http://dx.doi.org/10.1021/jo901297d

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117270
Deposited On:15 Apr 2021 10:49
Last Modified:15 Apr 2021 10:49

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