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 (2010) Ticl4 promoted menthyl ester chiral auxiliary mediated synthesis of chiral syn-β-amino esters and applications of a representative syn-β-amino ester Tetrahedron: Asymmetry, 21 (4). 385-392 . ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2010.02.010

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-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.

Item Type:Article
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ID Code:37270
Deposited On:25 Apr 2011 08:10
Last Modified:25 Apr 2011 08:10

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