- Preparation of stereoisomers of 3-sulfinylbutyric acid from (R)- and (S)-4-methyl-2-oxetanone
-
The β-lactone ((S) and (R)-4-methyl-2-oxetanone, 1, ent-1), readily available from (R)- and (S)-3-hydroxybutyric acid, is opened by sodium hydrosulfide, sodium alkane- and arenethiolates, respectively, with inversion of configuration. The resulting 3-(alkylthio)-2f, 2g, and 3-(arylthio)butyric acids, 2b-2e, ent-2h-2k (Table 1), oxidized with hydrogen peroxide in acetone to give the corresponding 3-(alkylsulfinyl)- and 3-(arylsulfinyl)butyric acids as mixtures of diastereoisomers 3b-3k and 4b-4k. These are separated and the pure like and unlike diastereoisomers isolated and fully characterized (Table 4). Configurational assignments rest upon a crystal structure analysis and comparison of properties in the two series.
- Breitschuh,Seebach
-
-
- Synthesis of Both Enantiomers of Optically Pure Saturated and α,β-Unsaturated γ-Substituted γ-Lactones from Chiral Sulphoxides. X-Ray Molecular structure of (3R,4S)-4-Methyl-4-t-butyl-3-(p-tolylthio)butanolide and of (3R,4R)-4-(Cyclohex-1-enyl)-4-methyl-3
-
The lithium carbanions of optically pure (+)-(R)-p-tolyl alkyl sulphoxides (5) reacted with lithium bromoacetate and gave (+)-(R)-3-(p-tolylsulphinyl)carboxylic acids (3).Their dimetallation produced a chiral homoenolate dianion equivalent (6) which added
- Albinati, Alberto,Bravo, Pierfrancesco,Ganazzoli, Fabio,Resnati, Giuseppe,Viani, Fiorenza
-
p. 1405 - 1416
(2007/10/02)
-