Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds |
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Authors: | Andrzej Wolan Mohamad SoueidanAngèle Chiaroni Pascal RetailleauSandrine Py Yvan Six |
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Institution: | a Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France b Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France |
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Abstract: | In this contribution, two methods are presented for the removal of benzyl-type protecting groups attached to the nitrogen atom of 2-azabicyclo3.1.0]hexane and 2-azabicyclo4.1.0]heptane systems. The first, based on the Polonovski reaction, is suitable for 3.1.0] systems. The second relies on an elimination process, starting from derivatives of O-methyl phenylglycinol, and is more general in terms of the substrates tolerated. Secondary bicyclic cyclopropylamines, including enantiomerically pure molecules, can thus be accessed. These compounds are then ready for further functionalisation. |
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Keywords: | Aminocyclopropanes Chiral auxiliaries Kulinkovich-de Meijere reaction Organotitanium chemistry Polonovski reaction |
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