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Synthesis of Tetrahydro‐1,2‐oxazines and Pyrrolidines via Cycloadditions of Donor–Acceptor Cyclobutanes and Nitrosoarenes
Author(s) -
Vemula Naresh,
Pagenkopf Brian L.
Publication year - 2015
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.201500542
Subject(s) - cyclobutanes , chemistry , lewis acids and bases , cycloaddition , regioselectivity , acceptor , catalysis , pyrrolidine , organic chemistry , combinatorial chemistry , medicinal chemistry , physics , condensed matter physics
During efforts to expand the scope of Lewis‐acid‐catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI 2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction.