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Using Nazarov Electrocyclization to Stage Chemoselective [1,2]‐Migrations: Stereoselective Synthesis of Functionalized Cyclopentenones
Author(s) -
Lebœuf David,
Huang Jie,
Gandon Vincent,
Frontier Alison J.
Publication year - 2011
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.201104870
Subject(s) - stereoselectivity , stage (stratigraphy) , chemistry , combinatorial chemistry , organic chemistry , catalysis , biology , paleontology
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.