150180-20-4

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 127196-21-8 (R)-(-)-methyl 4-phenyl-3-oxazolidineacetate 
• 941-69-5 N-phenyl-maleimide 
• 127196-24-1 4,6-Dioxo-5-phenyl-2-((R)-1-phenyl-2-trimethylsilanyloxy-ethyl)-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid methyl ester 

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.

High diastereofacial selectivity in the 1,3-dipolar cycloaddition of chiral azomethine ylides

Excellent diastereofacial and endo/exo stereoselectivities have been obtained in cycloaddition of the chiral azomethine ylide generated from 4-phenyloxazolidine acetic acid (-)-8-phenylmenthyl ester 1e.