90-26-6Relevant articles and documents
Eberhardt et al.
, p. 4365,4366,4367 (1974)
Base-controlled chemoselectivity: direct coupling of alcohols and acetonitriles to synthesise α-alkylated arylacetonitriles or acetamides
Bai, Liang,Ge, Min-Tong,Li, Chen,Qiu, Yuan-Rui,Wang, Ying,Xia, Ai-Bao,Xu, Dan-Qian
supporting information, p. 15200 - 15204 (2021/09/06)
We achieved chemoselective synthesis of α-alkylated arylacetonitriles and acetamides by combining Ir complex-catalysed direct coupling of alcohols and nitriles by a simple adjustment of the base. Methanol and ethanol performed well as the alkylating reagents. This method of acetonitrile alkylation provided a novel approach for carbon chain extension.
Lithium/DTBB-induced reduction of N-alkoxyamides and acyl azides
Yus, Miguel,Radivoy, Gabriel,Alonso, Francisco
, p. 914 - 918 (2007/10/03)
A series of N-alkoxyamides and N-methoxy-N-methylamides (Weinreb amides) have been subjected to dealkoxylation by reductive cleavage of the N-O bond with lithium powder and a catalytic amount of DTBB (10 mol%) at room temperature, leading to the corresponding amides. When the reaction is performed under reflux conditions, the corresponding alkanes, resulting from a formal deaminocarbonylation process, are obtained. This methodology applied to acyl azides furnished the corresponding primary amides.
Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst
Beard, Timothy,Cohen, Mark A.,Parratt, Julian S.,Turner, Nicholas J.,Crosby, John,Moilliet, Jock
, p. 1085 - 1104 (2007/10/02)
An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.
