Stereospecific [1,2]-rearrangement of a spirocyclic ammonium ylide with ring expansion sequence |
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Authors: | Antonio Saba |
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Affiliation: | Dipartimento di Chimica, Facoltà di Scienze, Via Vienna 2, I-07100 Sassari, Italy |
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Abstract: | Enantiomerically pure bicyclic 1,4-oxazepinone was obtained by the Cu(II)-catalyzed decomposition of an α-diazo carbonyl compound tethered to a chiral morpholinone, through the cascade evolution of the spirocyclic ammonium ylide formed. LiAlH4 reduction and transesterification of the lactone moiety of the oxazepinone afforded pure chiral pyrrolidine and 3-prolinone bicyclic hemiacetal, respectively, both bearing a quaternary stereocentre. |
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Keywords: | ammonium ylide carbenoid ring expansion rearrangement |
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