73828-17-8Relevant articles and documents
Ketoreductases in the synthesis of valuable chiral intermediates: Application in the synthesis of α-hydroxy β-amino and β-hydroxy γ-amino acids
Kambourakis, Spiros,Rozzell, J. David
, p. 663 - 669 (2004)
A general method for the synthesis of β-alkyl α-hydroxy β-amino and α- and γ-alkyl substituted β-hydroxy-γ- amino acids is described. The synthesis of all three classes of amino acids proceeds through a common chiral alcohol intermediate that is generated
17. Herstellung von erythro-2-Hydroxybernsteinsaure-Derivaten aus Apfelsaureester
Seebach, Dieter,Wasmuth, Daniel
, p. 197 - 200 (2007/10/02)
As a contribution to the much discussed diastereoselective synthesis of enantiomers of open chain compounds, >90percent erythro-selective branching of malic esters by alkylation of the doubly deprotonated derivative 2 (alkoxy-enolate) with methyl, allyl, and benzyl halides in THF at -78 deg (- 3aa, 3ba, 3bb, 3bc, Table 1) is described.A second alkylation (- 4) and addition of 2 to acetone (- 5) are also possible.Cyclization of 2 to the enantiomerically pure trans-epoxides 6 is achieved by treatment with iodine.Cuprate opening of 6b furnishes the same product 3ba obtained from the methylation of 2b, establishing the configurational assignment.
