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Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems
Author(s) -
Beppu Shota,
Arae Sachie,
Furusawa Masaki,
Arita Kosuke,
Fujimoto Hitoshi,
Sumimoto Michinori,
Imahori Tatsushi,
Igawa Kazunobu,
Tomooka Katsuhiko,
Irie Ryo
Publication year - 2017
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.201701481
Subject(s) - chemistry , enantioselective synthesis , cycloaddition , cinchonidine , benzofuran , cinchonine , intramolecular force , diastereomer , stereochemistry , furan , electrophile , stereoselectivity , asymmetric carbon , combinatorial chemistry , catalysis , organic chemistry , optically active
A base‐catalyzed stereoselective intramolecular dearomatizative [4+2] cycloaddition of o ‐phenylene‐linked ethynylnaphthol–benzofuran systems was explored. In this reaction, we presume the involvement of electrophilic vinylidene o ‐quinone methides (4π), which add across the electron‐rich furan double bonds (2π) to produce elaborate, fused oxa‐polyheterocyclic frameworks with consecutive quaternary and tertiary asymmetric carbon atoms as single diastereomers. The catalytic and enantioselective synthesis of these chiral fused polyheterocyclic structures is also feasible with the use of a prevalent cinchonidine or cinchonine chiral base.