725746-35-0Relevant academic research and scientific papers
Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP
Yu, Yang,Humeidi, Ranad,Alleyn, James R.,Doyle, Michael P.
, p. 8506 - 8513 (2017/08/23)
Allylic oxidation of heteroatom substituted cyclic alkenes by tert-butyl hydroperoxide (70% TBHP in water) using catalytic dirhodium caprolactamate [Rh2(cap)4] forms enone products with a variety of 2-substituted cyclic enamides and 3,4-dihyro-2H-pyrans. These reactions occur under mild reaction conditions, are operationally convenient to execute, and are effective for product formation with as low as 0.25 mol% catalyst loading. With heteroatom stabilization of the intermediate allylic free radical two sites for oxidative product formation are possible, and the selectivity of the oxidative process varies with the heteroatom when R = H. Cyclic enamides produce 4-piperidones in good yields when R = alkyl or aryl, but oxidation of 2H-pyrans also gives alkyl cleavage products. Alternative catalysts for TBHP oxidations show comparable selectivities but give lower product yields.
Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams
Pineschi, Mauro,Moro, Federica Del,Gini, Francesca,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 1244 - 1246 (2007/10/03)
For the first time, an excellent enantioselectivity has been obtained in the conjugate addition of hard organometallic reagents to α,β-unsaturated lactams bearing appropriate protecting-activating groups on the nitrogen.
