Synthesis of Tetrahydro‐1,2‐oxazines and Pyrrolidines via Cycloadditions of Donor–Acceptor Cyclobutanes and Nitrosoarenes | Zendy

Vemula Naresh | Zendy; Pagenkopf Brian L. | Zendy

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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.

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