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Pentamethylcyclopentadienyl rhodium(III)-chiral disulfonate hybrid catalysis for enantioselective C-H bond functionalization

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Title: Pentamethylcyclopentadienyl rhodium(III)-chiral disulfonate hybrid catalysis for enantioselective C-H bond functionalization
Authors: Satake, Shun Browse this author
Kurihara, Takumaru Browse this author
Nishikawa, Keisuke Browse this author
Mochizuki, Takuya Browse this author
Hatano, Manabu Browse this author
Ishihara, Kazuaki Browse this author
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Issue Date: Aug-2018
Publisher: Nature Publishing Group
Journal Title: Nature Catalysis
Volume: 1
Issue: 8
Start Page: 585
End Page: 591
Publisher DOI: 10.1038/s41929-018-0106-5
Abstract: Though Cp*Rh(III) complexes are prominent and versatile catalysts for C-H bond functionalization reactions, catalytic stereocontrol is difficult due to the lack of vacant coordination sites. Here, we report a hybrid strategy for inducing chirality without using previously reported chiral Cp-x ligands. A preformed hybrid catalyst, [Cp*RhLN][6,6'-Br-(S)-BINSate], catalysed C-H activation and subsequent conjugate addition of 2-phenylpyridine derivatives to enones in good yield and enantioselectivity (enantiomeric ratio up to 95:5). In addition to 2-phenylpyridines, the conjugate addition of 6-arylpurines proceeded with an enantiomeric ratio of up to 91:9 using [Cp*RhLN](R)-SPISate]. The results demonstrate that a chiral organic anion can efficiently control the enantioselectivity of Cp*Rh(III)-catalysed C-H bond functionalization without a chiral Cp-x ligand.
Type: article (author version)
URI: http://hdl.handle.net/2115/75059
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉野 達彦

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