Asymmetric synthesis of 1-azaspiro[4.5]decanes via intramolecular dipolar cycloaddition of nitrones containing the bornane-10,2-sultam chiral auxiliary |
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| Institution: | 1. School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia;2. Australian Centre for Research on Separation Science (ACROSS), University of Tasmania, Hobart, Tasmania 7001, Australia;1. Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan, 476000, People''s Republic of China;2. Henan Key Laboratory of Biomolecular Recognition and Sensing, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan, 476000, People''s Republic of China;1. Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale ‘A. Avogadro’, Largo Donegani 2/3, 28100 Novara (NO), Italy;2. Bracco Imaging spa, Bracco Research Centre, Via Ribes 5, 10010 Colleretto Giacosa (TO), Italy;3. Dipartimento di Biotecnologie Molecolari e Scienze per la Salute, Università degli Studi di Torino, Via Nizza 52, 10126 Torino (TO), Italy;1. Division of Basic Neuroscience, Medicinal Chemistry Program, McLean Hospital, Belmont, MA 02478, United States;2. Department of Psychiatry, Harvard Medical School, Boston, MA 02115, United States |
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| Abstract: | The intramolecular 1,3-dipolar cycloaddition of a cyclic nitrone, prepared by an asymmetric electrophilic enolate hydroxyamination using the (2R)-bornane-10,2-sultam chiral auxiliary, proceeds to give bridged and fused cycloadducts with total diastereocontrol. Reduction of the fused isoxazolidine provides a 1-azaspiro4.5]decane as a potential intermediate in the asymmetric synthesis of the cylindricine alkaloids. |
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