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

Goto, Takayuki; Natori, Yoshihiro; Takeda, Koji; Nambu, Hisanori; Hashimoto, Shunichi

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

Goto, Takayuki; Natori, Yoshihiro; Takeda, Koji et al.

Tetrahedron : Asymmetry, 2011, 22(8), 907-915

Permalink : https://hdl.handle.net/2115/46945

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アクセス権	open access
URI	https://hdl.handle.net/2115/46945
タイトル	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
著者	Goto, Takayuki ; Natori, Yoshihiro ; Takeda, Koji ; Nambu, Hisanori ; Hashimoto, Shunichi
著者名 Goto, Takayuki
著者名 Natori, Yoshihiro
著者名 Takeda, Koji
e-Rad_Researcher 80399956 著者名 Nambu, Hisanori
著者名 Hashimoto, Shunichi
言語	英語
発行日	2011-04-30
出版者	Elsevier
収録物名	Tetrahedron : Asymmetry
巻(号)	22(8)
ページ	907-915
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0957-4166
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.tetasy.2011.05.011