Eta3-pyranyl and eta3-pyridinyl molybdenum pi-complexes as chiral scaffolds for the enantioselective construction of substituted oxa- and aza[3.3.1]bicyclics: first enantio- and regiocontrolled [5+3] cycloaddition reactions |
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Authors: | Arrayás Ramón Gómez Liebeskind Lanny S |
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Institution: | Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, GA 30322, USA. |
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Abstract: | The first Mo-mediated 5+3] cycloadditions are reported. 3-Substituted pyranyl and pyridinyl molybdenum pi-complexes participate in enantiocontrolled 5+3] cycloadditions and provide a new and efficient synthetic approach to oxa- and aza3.3.1]bicyclics of high enantiomeric purity. The reaction proceeds in good to excellent yields and with complete regio- and endo-selectivities; it diverts to a 2+3] cycloaddition pathway when 2-substituted heterocycle pi-complexes are used. This methodology, coupled with a variety of general demetalation protocols, holds much promise in synthetic applications. |
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