145576-97-2Relevant academic research and scientific papers
New methodology for the synthesis of unsaturated 8-, 9- and 10-membered lactams
Evans, P. Andrew,Holmes, Andrew B.,McGeary, Ross P.,Nadin, Alan,Russell, Keith,O'Hanlon, Peter J.,Pearson, Neil D.
, p. 123 - 138 (2007/10/03)
Unsaturated 8-, 9- and 10-membered medium ring lactams 1 (n = 1, 2, 3) have been prepared in good yield by the Claisen rearrangement of the vinyl-substituted precursors 3 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
The example of a transoid amide (Imide) in an eight-membered lactam
Evans,Holmes,Collins,Raithby,Russell
, p. 2325 - 2326 (2007/10/02)
The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative as well as two unexpected products; the major product (resulting from a selenium re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide) with the largest p-orbital distortion (τ = 50.6°) recorded for a cyclic amide.
Regio- and Stereoselective Functionalisation of Monocyclic Medium Ring Lactams
Evans, P. Andrew,Collins, Ian,Hamley, Peter,Holmes, Andrew B.,Raithby, Paul R.,Russell, Keith
, p. 6859 - 6862 (2007/10/02)
The functionalisation of the potassium enolates of a series of racemic 7-, 8-, and 9-membered unsaturated lactams with trisyl azide and phenylselenyl chloride afforded the corresponding 3,n-disubstituted lactams with good stereoselectivities.
