150283-97-9Relevant academic research and scientific papers
Regio- and stereoselective reduction of bicyclic imides for the asymmetric synthesis of highly substituted pyrrolidines
Deprez,Royer,Husson
, p. 3781 - 3792 (2007/10/02)
1,3-dipolar cycloaddition of N-phenylmaleimide with azomethine ylides generated from α-aminonitrile or α-aminoester oxazolidines gave bicyclic imides, which were reduced regio- and stereoselectively to hydroxylactams. In the aminonitrile series, reduction with NaBH4/CeCl3 at low temperature gave a single hydroxylactam in high yield. In the aminoester series the regioselectivity was more dependent on the structure, and other conditions (LiBEt3H) were found to obtain a single hydroxylactam which corresponds to a reverse regiochemistry when compared with the aminonitrile series.
