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Highly Regio‐ and Stereoselective Dirhodium Vinylcarbene Induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/NO Cleavage and Rearrangement
Author(s) -
Wang Xiaochen,
Abrahams Quentin M.,
Zavalij Peter Y.,
Doyle Michael P.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201201917
Subject(s) - carbenoid , cycloaddition , regioselectivity , carbene , stereoselectivity , cleavage (geology) , chemistry , stereochemistry , nitrone , cascade , combinatorial chemistry , organic chemistry , catalysis , rhodium , biology , chromatography , paleontology , fracture (geology)
An abnormal cascade process provides a selective method for the preparation of tricyclic heterocycles. The cascade involves a metal carbene induced regioselective [3+2] cycloaddition, a Buchner reaction, and a [1,7]‐oxygen migration, which occurs with NO cleavage (see scheme). The products are formed with remarkable specificity.