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

Salvador Pérez-Estrada, Selene Lagunas-Rivera, María Elena Vargas-Díaz, Pedro Velázquez-Ponce, Pedro Joseph-Nathan, L. Gerardo Zepeda

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14 Scopus citations

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).

Original languageEnglish
Pages (from-to)1837-1843
Number of pages7
JournalTetrahedron Asymmetry
Volume16
Issue number10
DOIs
StatePublished - 23 May 2005

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