82575-10-8Relevant articles and documents
Synthesis of β-Lactones via a Spontaneous Intramolecular Cyclization of O-Lithiated Phenyl β-Hydroxyalkanoates Obtained by Aldolization of Ketones or Aldehydes with Lithium Enolates of Phenyl Esters
Wedler, Christine,Kunath, Annamarie,Schick, Hans
, p. 758 - 760 (2007/10/02)
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Dehydrative Decarboxylation of 2,3-Disubstituted 3-Hydroxycarboxylic Acids with Dimethylformamide Acetals - Mechanistic Studies and Preparative Applicability
Mulzer, Johann,Bruentrup, Gisela
, p. 2057 - 2075 (2007/10/02)
Dimethylformamide dimethylacetal (2a) converts the threo-3-hydroxycarboxylic acids 4 smoothly into the (E)/(Z)-olefins 7/6 only if R2 is an aryl or vinyl substituent.Althougt the reaction exhibits a distinct (E)-selectivity it cannot be considered as a stereo-controlled olefin synthesis.If R2 is alkyl, 2a generates the methyl esters 10 from 4.The erythro-acids 5 react with 2a to give 43 - 95percent of >98percent sterically pure 7.As the key tranformation on the multistep way from 4/5 to 6/7 the fragmentation of the zwitterionic intermediate 11/20 is postulated.