Enantioselective Synthesis of 2-Phenyl-9-oxabispidines

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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Breuning, M.; Winnacker, M.; Steiner, M. Eur. J. Org. Chem. 2007, 2100.