127253-91-2

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 101986-32-7 (-)-N-cyanomethyl-4-phenyl-1,3-oxazolidine 

Downstream Products

• 150283-96-8 (1S,3aS,6aR)-2-((R)-2-Hydroxy-1-phenyl-ethyl)-4,6-dioxo-5-phenyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carbonitrile 

Relevant academic research and scientific papers

Regio- and stereoselective reduction of bicyclic imides for the asymmetric synthesis of highly substituted pyrrolidines

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.

Asymmetric Synthesis XVII : Facile Generation of a Chiral Azomethine Ylide via the CN(R,S) Method

(-)-N-cyanomethyl-4-phenyl-1,3-oxazolidine, prepared in one step from R-(-)-phenylglycinol, gives a chiral azomethine ylide on treatment with TMSOTf and (iPr)2NEt.This ylide undergoes 1,3-dipolar cycloaddition reactions with activated olefins under very m