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Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O ‐Heterocycles
Author(s) -
Son Eun Chae,
Lee Jiseon,
Kim SungGon
Publication year - 2020
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.202000368
Subject(s) - chemistry , cycloaddition , intramolecular force , enone , michael reaction , alcohol , medicinal chemistry , base (topology) , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
Metal‐free and environmentally friendly synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This transformation was proposed to proceed through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Accordingly, morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively, in a highly diastereoselective manner.