Tetrahedron: Asymmetry

TiCl 4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester

M Periasamy, SS Ganesan, S Suresh

Index: Periasamy, Mariappan; Selva Ganesan, Subramaniapillai; Suresh, Surisetti Tetrahedron Asymmetry, 2010 , vol. 21, # 4 p. 385 - 392

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Citation Number: 10

Abstract

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- ...