| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5225167 | Tetrahedron | 2007 | 11 Pages |
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+.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
