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Synthesis of the 2-ethyl-3-methylsuccinic acids via a stereospecific malonic ester alkylation

✍ Scribed by F. F. van Leeuwen; A. Noordam; L. Maat; H. C. Beyerman

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
476 KB
Volume
99
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Reaction of (βˆ’)‐(S)‐methyl 2‐bromopropionate (4) (obtained from l‐alanine) with dibenzyl ethylmalonate gave stereospecifically in four steps ( + )‐(2__R__,3__S__)‐2‐ethyl‐3‐methylsuccinic acid (8a) and its diastereoisomer (8b). The malonic ester alkylation proceeded with Walden inversion. The chiroptical properties of the acids and the intermediates are in conformity with the known absolute configurations.

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