Catalytic Enantioselective Amination of Enolsilanes Using C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids
- 23 July 1999
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (4) , 595-598
- https://doi.org/10.1021/ol990113r
Abstract
[Cu(S,S)-t-Bu-box](OTf)2 (1) catalyzes the enantioselective amination of enolsilanes with azodicarboxylate derivatives. Isomerically pure enolsilanes of aryl ketones, acylpyrroles, and thioesters added to the azo-imide in greater than 95% ee. The use of an alcohol additive was critical to achieving catalyst turnover.Keywords
This publication has 7 references indexed in Scilit:
- Enantiospecific Synthesis of N-(9-Phenylfluoren-9-yl)-α-amino KetonesThe Journal of Organic Chemistry, 1997
- Synthetic Studies toward the Preparation of Phosphonate Analogs of Sphingomyelin and Ceramide 1-Phosphate Using Pentacovalent Organophospholene MethodologyThe Journal of Organic Chemistry, 1997
- The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenesJournal of the American Chemical Society, 1992
- [4 + 2] Cycloaddition reaction of dibenzyl azodicarboxylate and glycalsJournal of the American Chemical Society, 1989
- [4+2] Cycloaddition reaction of bis (trichloroethyl) azodicarboxylate and glycals: preparation of a C1-C1 2-amino disaccharideTetrahedron Letters, 1989
- A new facile diastereoconversion of 2-amino alcohols involving a novel cyclocarbamationTetrahedron Letters, 1987
- Photochemical reaction of imidazoles with unsaturated nitriles. Chemistry of encounter complex and ion pairThe Journal of Organic Chemistry, 1979