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Stereocontrolled synthesis of syn-?-Hydroxy-?-amino acids by direct aldolization of pseudoephenamine glycinamide.

ABSTRACT: ?-Hydroxy-?-amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of ?-hydroxy-?-amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one-flask protocol. Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldehyde or ketone substrate affords aldol addition products that are stereochemically homologous with L- or D-threonine, respectively. These products, which are typically solids, can be obtained in stereoisomerically pure form in yields of 55-98?%, and are readily transformed into ?-hydroxy-?-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction with sodium borohydride. This new chemistry greatly facilitates the construction of novel antibiotics of several different classes.

SUBMITTER: Seiple IB 

PROVIDER: S-EPMC4191905 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Stereocontrolled synthesis of syn-β-Hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide.

Seiple Ian B IB   Mercer Jaron A M JA   Sussman Robin J RJ   Zhang Ziyang Z   Myers Andrew G AG  

Angewandte Chemie (International ed. in English) 20140401 18

β-Hydroxy-α-amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of β-hydroxy-α-amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one-flask protocol. Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldeh  ...[more]

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