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Highly Diastereoselective Synthesis of Methylenecyclobutanes by Merging Boron‐Homologation and Boron‐Allylation Strategies
Author(s) -
Eisold Michael,
Didier Dorian
Publication year - 2015
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.201507444
Subject(s) - stereocenter , boron , stereoselectivity , adduct , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
A highly diastereoselective synthesis of methylenecyclobutanes possessing a quaternary stereocenter is reported, in which boron homologation of an easily‐generated cyclobutenylmetal species is performed, followed by an allylation reaction. Combining three steps in a one‐pot process further optimized the method, which afforded the expected adducts in excellent yields and stereoselectivity, starting from commercially available 4‐bromobutyne.