✦ LIBER ✦

The Stereoselective Synthesis of 2-Aryl-2-hydroxybutanoic Acid via Menthyl Chiral Auxiliaries

✍ Scribed by Ji-Ming Xiang; Bao-Lin Li

Publisher: John Wiley and Sons
Year: 2010
Tongue: German
Weight: 182 KB
Volume: 93
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.201000024

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✦ Synopsis

In the presence of titanium(IV) tetraethoxide ((EtO) 4 Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (À)-(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 Et 2 Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and 1 H-and 13 C-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.

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