3910-40-5Relevant 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
supporting information, 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.
Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media
Nelson, Amanda K.,Peck, Cheryl L.,Rafferty, Sean M.,Santos, Webster L.
, p. 4269 - 4279 (2016/06/09)
Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to aff
Stereoselective silylcupration of conjugated alkynes in water at room temperature
Linstadt, Roscoe T. H.,Peterson, Carl A.,Lippincott, Daniel J.,Jette, Carina I.,Lipshutz, Bruce H.
, p. 4159 - 4163 (2014/05/06)
Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology. Fast, cheap, and green: Micellar catalysis enables the selective construction of a variety β-silyl-substituted carbonyl derivatives under mild aqueous conditions. The reaction is catalyzed by low levels of CuI, is compatible with numerous electron-withdrawing groups, affords high yields, and provides opportunities for scale-up and recycling of the reaction medium. The environmental impact, as measured by E Factors, is very low.
