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Sociedade Brasileira de Química, SBQ, Journal of the Brazilian Chemical Society, 6(21), p. 1017-1036, 2010

DOI: 10.1590/s0103-50532010000600011

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Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone

Journal article published in 2010 by Visnovezky,Damian, Marcela Amongero, Amongero,Marcela, Damian Visnovezky, Teodoro S. Kaufman ORCID, Kaufman,Teodoro S.
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.