Simultaneous Generation and Subsequent Cycloaddition of  ortho ‐Quinonemethides and Cyclic Enecarbamates Promoted by a Gold/Lewis Acid Catalytic System | Zendy

Fernández Patricia | Zendy; Alonso Pedro | Zendy; Fañanás Francisco J. | Zendy; Rodríguez Félix | Zendy

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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.

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