120926-91-2Relevant articles and documents
The stereoselective synthesis of 2-aryl-2-hydroxybutanoic acid via menthyl chiral auxiliaries
Xiang, Ji-Ming,Li, Bao-Lin
experimental part, p. 2015 - 2022 (2010/12/25)
In the presence of titanium(IV) tetraethoxide ((EtO)4Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (-)-(1R,2S,5R)-menthol. Using menthyl as a chiral auxiliary, the corresponding novel (R)-menthyl 2-aryl-2-hydroxybutanoates are synthesized by the addition of Et2Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and 1H- and 13C-NMR spectroscopy, mass spectrometry, and elemental analysis. The diastereoselectivities are analyzed by HPLC. The addition reactions are completed with good yields and high diastereoisomeric excess (de up to 95%), and, after hydrolysis, the (R)-2-aryl-2-hydroxybutanoic acids are obtained with high optical purities.