AN ASYMMETRIC SYNTHESIS OF GLYCEROL DERIVATIVES BY THE ENANTIOSELECTIVE ACYLATION OF PROCHIRAL GLYCEROL
- 5 June 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 13 (6) , 949-952
- https://doi.org/10.1246/cl.1984.949
Abstract
Optically active glycerol derivatives are obtained in up to 84% e.e. by the selective acylation of the tin(II) alkoxides generated from 2-O-arylsulfonylglycerols and 1,1′-dimethylstannocene or (methylcyclopentadienyl)tin(II) chloride by the use of a chiral diamine derived from (S)-proline as a ligand.Keywords
This publication has 11 references indexed in Scilit:
- New nonenzymic chiral induction. A highly regioselective differentiation between two identical groups in meso-2,4-dimethylglutaric acidThe Journal of Organic Chemistry, 1983
- Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diolsJournal of the American Chemical Society, 1982
- Enantioselective synthesis of (-)-physostigmine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
- A Simple Synthesis of (R)-Glycerol Acetonide from Ascorbic AcidHETEROCYCLES, 1982
- Chirally selective synthesis of sugar moiety of nucleosides by chemicoenzymatic approach: L- and D-riboses, showdomycin, and cordycepinJournal of the American Chemical Society, 1981
- Total synthesis of (R)-glycerol acetonide and the antiepileptic and hypotensive drug (-)-.gamma.-amino-.beta.-hydroxybutyric acid (GABOB): use of vitamin C as a chiral starting materialJournal of the American Chemical Society, 1980
- Preparation of (R)- and (S)-mevalonic acidsJournal of the American Chemical Society, 1975
- Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) estersJournal of the American Chemical Society, 1973
- Requirements for Stereospecificity in Hydrolysis by α-Chymotrypsin. IV. The Hydroxyl Substituent. Absolute Configurations1Journal of the American Chemical Society, 1961
- Preparation of Saturated and Unsaturated Symmetrical MonoglyceridesJournal of the American Chemical Society, 1953