Elektrochemische Oxidation von (S)-Äpfelsäure-Derivaten: ein Weg zu enantiomerenreinen alkylierten Malonaldehydsäure-estern
✍ Scribed by Philippe Renaud; Marianne Hürzeler; Dieter Seebach
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- German
- Weight
- 415 KB
- Volume
- 70
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Electrochemical Oxidation of (S)-Malic-Acid Derivatives: a Route to Enantiomerically Pure Alkylmalonaldehydic Estcrs
The ?.?-di;ilkylinalic-acid diesters. prepared by the pi-eviously described diastereosclective alkylations through dilithiinn alkoxitic enolatea, ;ire s.ipoiiitled to thc rnonomtci-s conlaininp a free a-hydroxycarhoxylic-acid moiety iSdrm7c 31. The monoesters arc suhjected to electl-ocheinical oxidative decarboxy1,ition in MeOH. If the Intermediate monoacids ;ire purified, the iiialonclldchydic esters (2-forinyl-2-alkyIcarboxyl;iles) obraincd by this proccdure are enantioinerically pure; thcy have the s;iine sIructural features, i.t,. two cnantiotopic functionrili.mi branches on the (pcrsuhstituted) stercogenic center, iis the well known 3-hydroxy-2-nicthylpropaiioic acid ('Rorlir acid') which war employed frequently as il starting material f'or the prepar;ition of cither enantioiner of various target inolecules.