A Straightforward Synthesis of Enantiopure Bicyclic Azetidines

Enantiomerically pure 1‐azabicyclo[3.2.0]heptane derivatives were synthesized in a straightforward manner from readily available chiral sources, namely, enantiomerically pure epoxides and L‐proline. The key step of this synthesis relied on a diastereoselective intramolecular alkylation of a proline...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-12, Vol.2007 (34), p.5734-5739
Main Authors: Sivaprakasam, Mangaleswaran, Couty, François, David, Olivier, Marrot, Jérôme, Sridhar, Regati, Srinivas, Boga, Rama Rao, Kakulapati
Format: Article
Language:English
Subjects:
Bicyclic compounds
Fused-ring systems
Nitrogen heterocycles
Strained molecules
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Summary:Enantiomerically pure 1‐azabicyclo[3.2.0]heptane derivatives were synthesized in a straightforward manner from readily available chiral sources, namely, enantiomerically pure epoxides and L‐proline. The key step of this synthesis relied on a diastereoselective intramolecular alkylation of a proline enolate, which led to an azetidine ring fused to a five‐membered ring. These strained bicyclic nitrogen derivatives were found to be good precursors for the preparation of azepanes, after transformation into the corresponding ammonium trifluoromethanesulfonates followed by reaction with nucleophiles.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700616