1293389-84-0Relevant academic research and scientific papers
TiCl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester
Periasamy, Mariappan,Selva Ganesan, Subramaniapillai,Suresh, Surisetti
experimental part, p. 385 - 392 (2010/06/21)
β-Amino esters were obtained in up to 78% yield with 72:28-96:4 diastereomeric ratios by the reaction of the chiral titanium enolate of menthyl esters, prepared using the TiCl4/Et3N reagent system with prochiral imines. A representative syn-β-amino ester derivative has been used for the resolution of racemic mandelic acid to obtain a sample with >99% ee in a single step. A representative syn-β-amino ester was converted to the corresponding N-deprotected amino ester using the Pd-C/HCOOH reagent system, and then to the corresponding β-amino acid using the glacial CH3COOH/HCl reagent system, and to the corresponding β-lactam derivative with partial epimerization by the reaction using C2H5MgBr.
