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Catalytic enantioselective C-H functionalization of indoles with α-diazopropionates using chiral dirhodium(II) carboxylates : asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A
| Title: | Catalytic enantioselective C-H functionalization of indoles with α-diazopropionates using chiral dirhodium(II) carboxylates : asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A |
| Authors: | Goto, Takayuki Browse this author | | Natori, Yoshihiro Browse this author | | Takeda, Koji Browse this author | | Nambu, Hisanori Browse this author →KAKEN DB | | Hashimoto, Shunichi Browse this author |
| Issue Date: | 30-Apr-2011 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron : Asymmetry |
| Volume: | 22 |
| Issue: | 8 |
| Start Page: | 907 |
| End Page: | 915 |
| Publisher DOI: | 10.1016/j.tetasy.2011.05.011 |
| Abstract: | An enantioselective C-H functionalization of N-methoxymethyl (MOM)-protected 2,3-unsubstituted indoles with α-diazopropionates has been effected under catalysis by dirhodium(II) tetrakis[N-phthaloyl-(S)-triethylalaninate], Rh2(S-PTTEA)4, providing α-methyl-3-indolylacetates in high yields and with enantioselectivities of up to 86% ee. The effectiveness of this protocol was demonstrated by the first catalytic asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A, a potent plant-growth inhibitor. Furthermore, the Fujioka protocol using a combination of TMSOTf and 2,2'-bipyridyl was shown to be superior for the removal of the N-MOM group. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/46945 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 南部 寿則
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