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ChemInform Abstract: Asymmetric Oxidative Dimerization of the Enolates of N-(Bis(methylthio) methylene)- and N-(Diphenylmethylene)glycine Esters.

✍ Scribed by C. ALVAREZ-IBARRA; A. G. CSAKY; B. COLMENERO; M. L. QUIROGA

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199736234

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✦ Synopsis

Asymmetric Oxidative Dimerization of the Enolates of N-(Bis(methylthio) methylene)-and N-(Diphenylmethylene)glycine Esters. -A new method for the synthesis of threo 3-aminoaspartates such as (II) via asymmetric oxidative dimerization of title compounds such as (I) is presented. The stereochemical outcome of the dimerization depends strongly on the starting material and the deprotonation conditions. The deprotonation with Li bases favors the formation of the threo products. The use of KOtBu affords (II) and the erythro compounds in ratios corresponding to a thermodynamic control.

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