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Cycloaddition Reaction of Mesoionic 4‐Trifluoroacetyl‐1,3‐oxazolium‐5‐olates with Enamines Affording 2‐Trifluoroacetylpyrroles
Author(s) -
Saijo Ryosuke,
Kawase Masami
Publication year - 2019
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.201801728
Subject(s) - mesoionic , chemistry , cycloaddition , trifluoroacetic anhydride , trifluoroacetic acid , yield (engineering) , 1,3 dipolar cycloaddition , azomethine ylide , medicinal chemistry , enamine , organic chemistry , catalysis , materials science , metallurgy
Mesoionic 4‐trifluoroacetyl‐1,3‐oxazolium‐5‐olates (münchnones) reacted with enamines to yield densely functionalized 2‐trifluoroacetylpyrroles. The trifluoroacetic acid addition in the reaction was the key for the good yields of the 1,3‐dipolar cycloaddition product. DFT calculations were performed for the 1,3‐dipolar cycloadditions between münchnones and enamines.