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Nickel‐Catalyzed Chemo‐ and Stereoselective Alkenylative Cyclization of 1,6‐Enynes with Alkenyl Boronic Acids
Author(s) -
Yang ChunMing,
Mannathan Subramaniyan,
Cheng ChienHong
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302180
Subject(s) - stereoselectivity , catalysis , nickel , chemistry , toluene , sulfonate , cyclooctadiene , organic chemistry , combinatorial chemistry , computer science , sodium
Discover nickel! A nickel‐catalyzed alkenylative cyclization of 1,6‐enynes and alkenyl boronic acids affording substituted pyrrolidines and dihydrofurans is described (see scheme; cod=1,5‐cyclooctadiene, Ts = p ‐toluene sulfonate). The reaction is highly chemo‐ and stereoselective. A possible reaction mechanism involving a nickelacyclopentene intermediate is proposed.