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Diastereoselective Cyclobutenol Synthesis: A Heterogeneous Palladium‐Catalyzed Oxidative Carbocyclization‐Borylation of Enallenols
Author(s) -
Li ManBo,
Posevins Daniels,
Gustafson Karl P. J.,
Tai CheukWai,
Shchukarev Andrey,
Qiu Youai,
Bäckvall JanE.
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.201805118
Subject(s) - borylation , palladium , catalysis , chemistry , selectivity , oxidative phosphorylation , combinatorial chemistry , kinetic resolution , heterogeneous catalysis , organic chemistry , enantioselective synthesis , aryl , biochemistry , alkyl
A highly selective and efficient oxidative carbocyclization/borylation of enallenols catalyzed by palladium immobilized on amino‐functionalized siliceous mesocellular foam (Pd‐AmP‐MCF) was developed for diastereoselective cyclobutenol synthesis. The heterogeneous palladium catalyst can be recovered and recycled without any observed loss of activity or selectivity. The high diastereoselectivity of the reaction is proposed to originate from a directing effect of the enallenol hydroxyl group. Optically pure cyclobutenol synthesis was achieved by the heterogeneous strategy by using chiral enallenol obtained from kinetic resolution.