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Synthesis 2007(11): 1702-1706  
DOI: 10.1055/s-2007-966040
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of 2-Phenyl-9-oxabispidines

Matthias Breuning*, Melanie Steiner
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)8884755; e-Mail: breuning@chemie.uni-wuerzburg.de;
Further Information

Publication History

Received 9 January 2007
Publication Date:
02 May 2007 (online)

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Abstract

A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichlorohydrin to the corresponding cis-2,6-bis(hydroxymethyl)-substituted morpholine intermediate, and final cyclization with a primary amine delivered the desired 2-phenyl-9-oxabispidines in good yields. The substituents at the nitrogen atoms were varied by de­benzylation and subsequent alkylation.

Key words

9-oxabispidines - stereoselective synthesis - bicyclic compounds - heterocycles - sparteine

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