Highly Regio‐ and Stereoselective Dirhodium Vinylcarbene Induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/NO Cleavage and Rearrangement | Zendy

Wang Xiaochen | Zendy; Abrahams Quentin M. | Zendy; Zavalij Peter Y. | Zendy; Doyle Michael P. | Zendy

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Highly Regio‐ and Stereoselective Dirhodium Vinylcarbene Induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/NO 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.

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