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Synfacts 2006(11): 1143-1143  
DOI: 10.1055/s-2006-949429
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Epoxyhydroxylamines and 1,2-Oxazetidines

Contributor(s): Mark Lautens, Frédéric Ménard
V. Capriati, S. Florio*, R. Luisi, A. Salomone, C. Cuocci
Universita di Bari, Istituto di Chimica dei Composti Organometallici and Istituto di Crystallografia, Bari, Italy
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

The report describes a rapid method to prepare enantiopure epoxyhydroxylamines 3 and 1,2-oxazetidines 4 from chiral epoxides. The success of the method is important in that the corresponding reaction was reported not to work with carbonyl moieties (by the same authors). The densely functionalized hydroxylamines 3 undergo a regioselective epoxide opening in basic conditions to form the sterically congested 4. None of the 5-endo product 5 was observed. Noteworthy is that the oxazetidines 4 are stable and can be isolated by chromatography.