Radical carboazidation: Expedient assembly of the core structure of various alkaloid families

P Panchaud, C Ollivier, P Renaud…

Index: Panchaud, Philippe; Ollivier, Cyril; Renaud, Philippe; Zigmantas, Sarunas Journal of Organic Chemistry, 2004 , vol. 69, # 8 p. 2755 - 2759

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Citation Number: 72

Abstract

A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is ...