292615-60-2Relevant academic research and scientific papers
On the diastereoselectivity of alkylations of bicyclic lactams
Bailey, Jonathan H.,Byfield, Andrew T.J.,Davis, Philip J.,Foster, Alison C.,Leech, Michael,Moloney, Mark G.,Mueller, Matthias,Keith Prout
, p. 1977 - 1982 (2007/10/03)
The diastereoselectivity in the alkylation of the enolates of bicyclic lactams 2 derived from pyroglutaminol la has been found to depend upon the nature of the hemiaminal ether protecting group. Although exo-alkylation has been widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is postulated that this is a result of the opening of the bicyclic structure of the enolate derived from 2d, and the consequent stereoelectronic facilitation of endo-facial attack.
