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Synthesis 2011(7): 1113-1119  
DOI: 10.1055/s-0030-1258464
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-8-Oxa-3-azabicyclo[3.2.1]octan-2-thione and (±)-2-Oxa-5-azabicyclo[2.2.1]heptan-6-thione: Potential Synthons for the Preparation of Novel Heteroaryl-Annulated Bicyclic Morpholines

Daniel P. Walker*, Donn G. Wishka, Paul Beagley, Gemma Turner, Nicola Solesbury
Pfizer Global Research & Development, Eastern Point Road, Groton, CT 06340, USA
Fax: +1(860)6860013; e-Mail: daniel.p.walker@pfizer.com;
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Publication History

Received 13 December 2010
Publication Date:
08 March 2011 (online)

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Abstract

The bridged bicyclic morpholinethiones (±)-8-oxa-3-azabicyclo[3.2.1]octane-2-thione and (±)-2-oxa-5-azabicyclo[2.2.1]heptane-6-thione have been prepared in five and eight steps, respectively. Both compounds were derived from a respective requisite cis-disubstituted tetrahydrofuran, which was stereoselectively prepared via hydrogenation of the corresponding disubstituted furan derivatives.

Key words

stereoselective synthesis - heterocycles - bicyclic compounds - furans - hydrogenation

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