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Iodocarbamation of N ‐Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan‐2‐ones
Author(s) -
Quinodoz Pierre,
Quelhas Alexandre,
Wright Karen,
Drouillat Bruno,
Marrot Jérôme,
Couty François
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700231
Subject(s) - stereoselectivity , chemistry , electrophile , palladium , iodine , coupling reaction , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis
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.