Iodocarbamation of N‐Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan‐2‐ones. Issue 18 (12th May 2017)

• Record Type: Journal Article
• Authors: Quinodoz, Pierre; Quelhas, Alexandre; Wright, Karen; Drouillat, Bruno; Marrot, Jérôme; Couty, François
• Is Part Of: European journal of organic chemistry. Issue 18(2013)
• Page Start: 2621
• Page End: 2626
• Publication Date: 2017-05-12
• Subjects: Halocarbamation -- Iodine -- Heterocycles -- Cyclization -- Cross‐coupling -- Carbamates; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700231
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient and general iodocarbamation of benzyl N ‐homopropargylcarbamates has been developed by using iodine as the electrophilic agent. This regio‐ and stereoselective cyclization yielded ( E )‐6‐iodomethyleneoxazinan‐2‐ones, which can be further transformed through palladium cross‐coupling reactions followed by hydrogenation to produce 1, 3‐oxazinan‐2‐ones. Abstract : The iodocarbamation of N ‐Cbz‐homopropargylamines gives high yields of stereodefined 6‐iodomethyleneoxazin‐2‐ones that can be further transformed into oxazinan‐2‐ones.