243665-13-6Relevant articles and documents
General Method for the Preparation of Indole-2-Weinreb Amides
Glas, Carina,Bracher, Franz
, p. 757 - 768 (2019/01/23)
Indole-2-Weinreb amides are obtained via thermolysis of α-azidocinnamic acid Weinreb amides in a Hemetsberger-Knittel-type cyclization. The required vinyl azides are not accessible by Knoevenagel condensation, but are obtained by cerium(IV)-mediated oxida
Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: A Powerful Synthetic Platform
Drissi-Amraoui, Sammy,Morin, Marie S. T.,Crévisy, Christophe,Baslé, Olivier,Marciadefigueiredo, Renata,Mauduit, Marc,Campagne, Jean-Marc
supporting information, p. 11830 - 11834 (2015/10/05)
An efficient copper-catalyzed enantioselective conjugate addition of dimethylzinc to α,β- and α,β,γ,δ-unsaturated 2-acyl-N-methylimidazoles has been achieved using a chiral bidentate hydroxyalkyl-NHC ligand. The reactions proceeded with both excellent regio- and enantioselectivity (14 examples, 87-95 % ee) to afford the desired 1,4-adducts, which were easily transformed to the corresponding aldehydes, esters, and ketones. Subsequently, this powerful methodology was therefore successfully applied in the synthesis of natural products. Furthermore, an iterative process was also disclosed leading to highly desirable 1,3-desoxypropionate skeletons (up to 94 % d.e.). The enantioselective conjugate addition of dimethylzinc to (poly)unsaturated 2-acyl-N-methylimidazoles proceeds under Cu catalysis with excellent regio- and enantioselectivities (up to 95 % ee). The resulting 1,4-adducts can be easily transformed to the corresponding aldehydes, esters, ketones, and amines. This methodology was successfully applied in the synthesis of 1,3-desoxypropionate subunits and natural products.
Vinyl Weinreb amides: A versatile alternative to vinyl ketone substrates for the Heck arylation
Baker, David B.,Gallagher, Peter T.,Donohoe, Timothy J.
, p. 3690 - 3697 (2013/05/08)
This paper describes the use of unsaturated Weinreb amides as excellent substrates for the Heck reaction. Subsequent derivatization of the products with organometallic reagents allowed access to a variety of substituted vinyl ketones that could not have been prepared directly via Heck reaction on unsaturated ketone precursors.
