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Highly Substituted Furo[3,4-d][1,2]oxazines: Gold-Catalyzed Regiospecific and Diastereoselective 1,3-Dipolar Cycloaddition of 2-(1-Alkynyl)-2-alken-1-ones with Nitrones

Authors

  • Feng Liu,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039
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  • Yihua Yu Prof.,

    1. Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University (P.R. China)
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  • Junliang Zhang Prof. Dr.

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P.R. China)
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  • Financial support from the National Natural Science Foundation of China (20702015), the Science and Technology Commission of Shanghai Municipality (07DZ22937), Shanghai Shuguang Program (07SG27), Shanghai Pujiang Program (07pj14039), and Shanghai Leading Academic Discipline Project (B409) is greatly appreciated.

Abstract

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Doppelter Ringschluss: Die Gold(I)-katalysierte 1,3-dipolare Cycloaddition von 2-(1-Alkinyl)-2-alken-1-onen mit Nitronen unter milden Bedingungen öffnet einen einfachen, regiospezifischen und stereoselektiven Zugang zu hoch substituierten Furo[3,4-d][1,2]oxazinen (siehe Schema). Diese kondensierten Heterobicyclen lassen sich leicht in Furane oder 3,6-Dihydro-2H-1,2-oxazine umwandeln.

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