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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
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)
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Submitter: 澤村 正也
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