Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

…, P Velázquez-Ponce, P Joseph-Nathan…

Index: Perez-Estrada, Salvador; Lagunas-Rivera, Selene; Vargas-Diaz, Maria Elena; Velazquez-Ponce, Pedro; Joseph-Nathan, Pedro; Zepeda, L. Gerardo Tetrahedron Asymmetry, 2005 , vol. 16, # 10 p. 1837 - 1843

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Citation Number: 7

Abstract

The enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids was achieved by using 2-acyloxathianes 1a–c and the mixed acyl-S, O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(−)-myrtenal. This procedure allowed the preparation of the title compounds in> 95% enantiomeric excess (ee).