Asymmetric Synthesis with Sugar Derivatives. III. Action of Methylmagnesium Iodide on Sugar Esters of Phenylglyoxylic Acid
- 1 September 1967
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 40 (9) , 2168-2171
- https://doi.org/10.1246/bcsj.40.2168
Abstract
Asymmetric synthesis of atrolactic acid was investigated by the reaction of methylmagnesium Iodide with phenylglyoxylic ester containing such an optically active component as 1,2 ; 5,6-di-O-cyclohexylidene-d-glucose, its isopropylidene derivative 5-O-ethyl-1,2-O-isopropylidene-d-xylose, its 5-deoxy-5-S-ethyl derivative, or 5-deoxy-1,2-O-isopropylidene-d-xylose. All of the resulting sugar atrolactates were very easily hydrolyzed with alkali at room temperature to afford the levorotatory acid in 22–38% optical yield. The asymmetric reactions proceeded in accordance with Prelog’s rule, but a Prelog’s scheme for asymmetric induction was slightly modified when the steric course for 3-O-phenylglyoxyloyl-1,2 ; 5,6-di-O-cyclohexylidene- and -isopropylidene-d-glucose was discussed.This publication has 20 references indexed in Scilit:
- Studies in Stereochemistry. XXXII. Models for 1,2-Asymmetric InductionJournal of the American Chemical Society, 1963
- Asymmetric Induction Studies with Optically Active Biphenyls. The Reactions of Phenylglyoxylates of the Phenyldihydrothebaine Series with Methylmagnesium Iodide1Journal of the American Chemical Society, 1958
- Reaktionen mit Mikroorganismen. 7. Mitteilung. Die Bestimmung der absoluten Konfiguration von (+)‐trans, trans‐Dekalol‐(1) durch asymmetrische SyntheseHelvetica Chimica Acta, 1958
- Die Bestimmung der absoluten Konfiguration von (—)‐Dinaphto‐2′,1′:1,2;1″,2″:3,4‐cycloheptadienol‐(6), eines atropisomeren Enantiomeren, durch asymmetrische Atrolactinsäure‐SyntheseHelvetica Chimica Acta, 1958
- The Configuration of Atrolactic Acid. Retention of Configuration in the Acid-catalyzed Ring Opening of Stilbene Oxides1Journal of the American Chemical Society, 1956
- Untersuchungen über asymmetrische Synthesen III. Über die Anwendung der asymmetrischen Synthese zur Konfigurationsbestimmung bei Triterpenen und SteroidenHelvetica Chimica Acta, 1953
- Untersuchungen über asymmetrische Synthesen II. Über den sterischen Verlauf der Umsetzung von Phenylglyoxylsäure‐estern des Menthols, Neomenthols, Borneols und Isoborneols mit MethylmagnesiumjodidHelvetica Chimica Acta, 1953
- The Preparation and Proof of Structure of 1,2:5,6-Dicyclohexylidene-D-glucofuranoseJournal of the American Chemical Society, 1949
- LXXX.—Experiments on the Walden inversion. Part IV. The interconversion of the optically active phenylmethylglycollic acidsJournal of the Chemical Society, Transactions, 1910
- CXXVII.—Studies in asymmetric synthesis. I. Reduction of menthyl benzoylformate. II. Action of magnesium alkyl haloids on menthyl benzoylformateJournal of the Chemical Society, Transactions, 1904