1415345-58-2Relevant academic research and scientific papers
Asymmetric Kinugasa reaction involving six-membered cyclic nitrones
Grzeszczyk, Barbara,Po?awska, Kamila,Shaker, Yasser M.,Stecko, Sebastian,Mames, Adam,Wo?nica, Magdalena,Chmielewski, Marek,Furman, Bart?omiej
, p. 10633 - 10639 (2012)
Kinugasa reactions between terminal acetylenes and six-membered ring nitrones when one or both components are chiral, proceed in a low to moderate yield and with a high diastereoselectivity affording mostly one, dominant β-lactam product. The first step of the reaction is controlled by the configuration of the nitrone, whereas the protonation of the C-7 center of the carbacepham skeleton in the second step depends on: a) the configuration of the bridgehead carbon atom formed in the first step, b) epimerization process in the presence of a base, and c) on the configuration of the stereogenic center in the acetylenic partner. In the case of the nitrone derived from dihydroisoquinoline, the reaction proceeds in a more complex way affording not only β-lactams, but also products derived from the alternative regio-1,3-cycloaddition, or nucleophilic addition of the acetylene to the double bond of the nitrone.
