22464-06-8Relevant academic research and scientific papers
Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions
Miaskiewicz, Solène,Reed, John H.,Donets, Pavel A.,Oliveira, Caio C.,Cramer, Nicolai
, p. 4039 - 4042 (2018/03/13)
Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.
Development of biisoquinoline-based chiral diaminocarbene ligands: Enantioselective SN2′ allylic alkylation catalyzed by copper-carbene complexes
Seo, Hwimin,Hirsch-Weil, Dimitri,Abboud, Khalil A.,Hong, Sukwon
, p. 1983 - 1986 (2008/09/19)
Chiral biisoquinoline-based diaminocarbene ligands (BIQ) were designed to create a chiral environment extended toward the metal center, which was confirmed by an X-ray structure. The concise ligand synthesis is highlighted by a modified Bischler-Napieralski cyclization of bisamides prepared from readily available chiral phenethylamines, and allows easy variation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective SN2′ allylic alkylation with Grignard reagents showing SN2′ regioselectivity higher than 5:1 and enantioselectivity in the range of 68-77% ee.
