Using Nazarov Electrocyclization to Stage Chemoselective [1,2]‐Migrations: Stereoselective Synthesis of Functionalized Cyclopentenones
- 26 September 2011
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 50 (46), 10981-10985
- https://doi.org/10.1002/anie.201104870
Abstract
Highly functionalized cyclopentenones have been prepared stereospecifically through a chemoselective copper(II)‐mediated Nazarov/Wagner–Meerwein rearrangement sequence. After the initial 4π electrocyclization, this reaction involves two sequential [1,2]‐migrations depending upon both migratory ability and steric bulk of the substituents at C1 and C5 (see scheme). The proposed mechanism of the reaction is supported by DFT studies.Keywords
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