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Lewis Acid Catalyzed Intramolecular [4+2] Cycloaddition of In Situ Generated Aza‐Quinone Methides for the Stereoselective Synthesis of Furo/pyrano[3,2‐ c ]tetrahydroquinolines
Author(s) -
Gharpure Santosh J.,
Vishwakarma Dharmendra S.
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.201901598
Subject(s) - chemistry , stereoselectivity , intramolecular force , cycloaddition , olefin fiber , lewis acids and bases , catalysis , quinone methide , stereochemistry , quinone , in situ , medicinal chemistry , organic chemistry
The TMSOTf catalyzed intramolecular [4+2] cycloaddition of in situ generated aza‐ o ‐quinone methide allows an expedient, stereoselective access to cis/trans ‐fused furo/pyrano[3,2‐ c ]tetrahydroquinolines with excellent yields and diastereoselectivity. The geometry of the dienophile olefin was found to have a profound effect on the stereochemical outcome of these reactions.