Catalytic and asymmetric Friedel-Crafts alkylation of indoles with nitroacrylates. Application to the synthesis of tryptophan analogues |
| |
| Authors: | Yong Sui Li Liu Jun-Ling Zhao Dong Wang |
| |
| Affiliation: | a Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China
b Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100080, PR China |
| |
| Abstract: | An asymmetric Friedel-Crafts alkylation of indoles with nitroacrylates catalyzed by chiral (4R,5S)-DiPh-BOX (L1)-Cu(OTf)2 complex (10 mol %) has been developed. The reactions provide tryptophan nitro-precursors in moderate diastereoselectivities (anti/syn up to 72:28) and good to excellent enantioselectivities (up to 99% ee). The alkylation products could be easily reduced to optically active tryptophan analogues with Zn/H+. |
| |
| Keywords: | Catalytic and asymmetric Friedel-Crafts alkylation Chiral DiPhBOX-Cu(II) complex Indole Nitroacrylate Tryptophan |
| 本文献已被 ScienceDirect 等数据库收录！ |
