190605-07-3Relevant academic research and scientific papers
Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
Amongero, Marcela,Visnovezky, Damian,Kaufman, Teodoro S.
experimental part, p. 1017 - 1036 (2010/10/21)
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 DC
Catalytic asymmetric synthesis using feedstocks: An enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes
Smith, Craig R.,Babu, T.V. Rajan
experimental part, p. 3066 - 3072 (2009/08/08)
A three-step procedure for the synthesis of 2-arylpropionic acids (profens) from vinyl arenes in nearly enantiomerically pure form has been developed. Excellent yields (>97%), regioselectivities (>99%), and enantioselectivities (>97% ee) for the desired branched products were obtained in the asymmetric hydrovinylation reactions of vinyl arenes, and the products from these reactions were transformed into 2-arylpropionic acids via oxidative degradation. Subsequent Curtius or Schmidt rearrangements of these acids provided highly valued 1-arylethyl amines, including a prototypical primary amine with an α-chiral tertiary N-alkyl group, in very good yields.
