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Simultaneous Generation and Subsequent Cycloaddition of ortho ‐Quinonemethides and Cyclic Enecarbamates Promoted by a Gold/Lewis Acid Catalytic System
Author(s) -
Fernández Patricia,
Alonso Pedro,
Fañanás Francisco J.,
Rodríguez Félix
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.201800679
Subject(s) - chemistry , cycloaddition , lewis acids and bases , catalysis , lewis acid catalysis , enamine , pyrrole , combinatorial chemistry , quinone methide , boron trifluoride , reactive intermediate , organic chemistry , medicinal chemistry , quinone
A new catalytic reaction to synthesize structurally complex hexahydrochromeno[2,3‐ b ]pyrrole derivatives from simple 3‐butynamine and 2‐(hydroxymethyl)phenol derivatives is described. The process is promoted by a dual catalytic system formed by a gold complex and a Lewis acid (boron trifluoride). The reaction involves the synchronized transformation of the starting materials into two reactive intermediates, a cyclic enamine derivative and an ortho ‐quinone methide, that subsequently react between them through a formal [4+2] cycloaddition to furnish the final poly‐heterocyclic product in a straightforward way.