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Assembly of Trifluoromethylated Morpholines through Cascade Reactions of Bromoenones with Secondary Amino Alcohols
Author(s) -
Rulev Alexander Yu.,
Romanov Alexey R.,
Kondrashov Evgeniy V.,
Ushakov Igor A.,
Muzalevskiy Vasiliy M.,
Nenajdenko Valentine G.
Publication year - 2018
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.201800659
Subject(s) - chemistry , morpholine , moiety , oxetane , stereoselectivity , bicyclic molecule , stereochemistry , ring (chemistry) , organic chemistry , catalysis
Fluorinated α‐bromoenones react readily with amino alcohols containing a secondary amino group to give monocyclic morpholine derivatives or unexpected bicyclic compounds containing a morpholine moiety fused with an oxetane ring. The reactions are highly stereoselective. The assembly of these heterocycles starts with an aza‐Michael addition followed by intermolecular substitution and addition processes.