2024-03-28T15:34:14Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/469452022-11-17T02:08:08Zhdl_2115_20044hdl_2115_124Catalytic 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 AGoto, TakayukiNatori, YoshihiroTakeda, Koji1000080399956Nambu, HisanoriHashimoto, Shunichiopen access499An 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.Elsevier2011-04-30engjournal articleAMhttp://hdl.handle.net/2115/46945https://doi.org/10.1016/j.tetasy.2011.05.0110957-4166Tetrahedron : Asymmetry228907915https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/46945/1/TetA22-8_907-915.pdfapplication/pdf390.41 KB2011-04-30