An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates

Yevhenii M. Sokolenko^a^{, b}, Eugeniy N. Ostapchuk^a^{, b}, Artem Artemenko^b, Oleksandr O. Grygorenko*^a

^aTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
^bEnamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine Email: gregor@univ.kiev.ua

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Publication History

Received: 02 February 2017

Accepted after revision: 21 March 2017

Publication Date:
13 April 2017 (eFirst)

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Abstract

An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale.

Key words

cycloaddition - bicyclic compounds - morpholine analogues - conformational restriction - pyrrolidines - oxygen heterocycles

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