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Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates Using a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes

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Title: Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates Using a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes
Authors: Yasuda, Yuto Browse this author
Ohmiya, Hirohisa Browse this author →KAKEN DB
Sawamura, Masaya Browse this author →KAKEN DB
Keywords: asymmetric catalysis
allylic substitution
synthetic methods copper catalysis
organoboron compounds
Issue Date: Jun-2018
Publisher: Georg Thieme Verlag
Journal Title: Synthesis-stuttgart
Volume: 50
Issue: 11
Start Page: 2235
End Page: 2246
Publisher DOI: 10.1055/s-0036-1591548
Abstract: Details of the Cu-catalyzed enantioselective allyl-allyl coupling reaction between allylboronates and (Z)-allylic phosphates using a new chiral N-heterocyclic carbene (NHC) ligand containing a phenolic hydroxy group are presented. The copper catalysis delivers enantioenriched chiral 1,5-dienes with a tertiary stereogenic center. Compatibility with various functional groups and the use of earth-abundant and relatively low-toxicity copper as a metal are attractive features of this protocol. The utility of the chiral phenol-NHC ligand for enantioselective copper catalysis with organoboron compounds is demonstrated and enantiodiscrimination models are discussed.
Rights: (c)2018 Georg Thieme Verlag KG
Type: article (author version)
URI: http://hdl.handle.net/2115/74534
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 澤村 正也

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