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Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp 3 )−H arylation
Author(s) -
Schmitz Alexander J.,
Ricke Alexander,
Oschmann Michael,
Verho Oscar
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806416
Subject(s) - cyclobutane , stereocenter , cyclobutanes , chemistry , stereochemistry , aryl , organic chemistry , enantioselective synthesis , alkyl , ring (chemistry) , catalysis
This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C−H functionalization approach. The developed synthetic route involved an 8‐aminoquinoline‐directed C(sp 3 )−H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to furnish a variety of cyclobutane products with three contiguous stereocenters. Moreover, it was shown that the 8‐aminoquinoline auxiliary could be effectively removed from the cyclobutane derivatives using an ozonolysis‐based cleavage method.