The Formal [4+3] Cycloaddition between Donor−Acceptor Cyclobutanes and Nitrones | Zendy

Andrew C. Stevens | Zendy; Cory Palmer | Zendy; Brian L. Pagenkopf | Zendy

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The Formal [4+3] Cycloaddition between Donor−Acceptor Cyclobutanes and Nitrones

Author(s) -

Andrew C. Stevens,

Cory Palmer,

Brian L. Pagenkopf

Publication year - 2011

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol200220d

Subject(s) - cyclobutanes , diastereomer , chemistry , cycloaddition , yield (engineering) , alkoxy group , stereochemistry , organic chemistry , catalysis , metallurgy , materials science , alkyl

The formal [4+3] cycloaddition of 2-alkoxy-1,1-dicarboxylate activated donor-acceptor cyclobutanes with nitrones is disclosed. The reaction forms structurally unique oxazepines in moderate to high yield with a wide scope of nitrones. In most cases either a diastereomeric mixture or a single diastereomer may be formed, depending on the reaction conditions.

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