%0 Generic %A Li, Qiong %A Yang, Shao-Bo %A Zhang, Zhihui %A Li, Lei %A Xu, Peng-Fei %D 2009 %T Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-Amino Acids: Application to the Synthesis of a Key Intermediate for Lactacystin %U https://acs.figshare.com/articles/dataset/Diastereo_and_Enantioselective_Synthesis_of_Hydroxy_Amino_Acids_Application_to_the_Synthesis_of_a_Key_Intermediate_for_Lactacystin/2876986 %R 10.1021/jo8023973.s007 %2 https://acs.figshare.com/ndownloader/files/4574848 %K Enantioselective %K Diastereo %K stereoselective %K excess %K diastereoselectivity %K Application %K Intermediate %K acid %K lithium %K enolate %K hydrolysis %K Lactacystin %K lactacystin %K recovery %K dr %K presence %K methodology %K enantiomeric %K equiv %K chloride %K Synthesi %K Nucleophilic %K aldehyde %K 7. %K ee %K acidic %K THF %K aldol adducts %K Hydroxy %K auxiliary %K tricyclic iminolactones 1 %K chiral auxiliaries 6 %K yield %K preparation %K isomers %K synthesis %K Acid %K hydroxy %X The development of a highly efficient and stereoselective methodology for the preparation of β-hydroxy-α-amino acids is described. Nucleophilic addition of enolates of tricyclic iminolactones 1a and 1b to aldehydes in the presence of 6 equiv of lithium chloride in THF at −78 °C leads to aldol adducts in good yield (63−86%) and high diastereoselectivity (up to >25:1 dr). Subsequently, hydrolysis of the aldol adducts under acidic conditions leads to the corresponding β-hydroxy-α-amino acids in good yields (up to 83%) and excellent enantiomeric excesses (99% ee) with good recovery yields of the chiral auxiliaries 6 and 7. This methodology was applied to the facile synthesis of the key intermediate for lactacystin along with several isomers. %I ACS Publications