Simplified Chiral Aminolysis of Prochiral σ-Symmetric Dicarboxylic Anhydrides with Sodium Salt of 4(S)-IPTT
- 5 February 1988
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 17 (2) , 381-384
- https://doi.org/10.1246/cl.1988.381
Abstract
Highly enantioselective chiral aminolysis of cis-4-cyclo-hexen-1,2-ylenebis(carboxylic acid) anhydride has been performed by employing sodium salt of 4(R)-isopropyl-1,3-thiazolidine-2-thione in THF-DMSO. Other chiral aminolyses of prochiral σ-symmetric dicarboxylic anhydrides such as cis-cyclobutan-1,2-ylenebis(carboxylic acid) anhydride, meso-2,4-dimethylglutaric anhydride, and 3- [(t-butyldimethylsilyl) oxy] glutaric anhydride were similarly investigated.This publication has 8 references indexed in Scilit:
- Synthesis of carbapenems with a sulfonyl group in the C-6 side-chain and their biological activity.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Highly diastereoselective alkylation onto 4-acetoxy-2-azetidinones employing tin(II) enolates of 3-acyl C-4-chiral 1,3-thiazolidine-2-thionesJournal of the American Chemical Society, 1986
- New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydesThe Journal of Organic Chemistry, 1986
- Utilization of sulfur-containing leaving group. 7. Highly selective nonenzymic chiral induction into 3-methylglutaric acid and cis-4-cyclohexen-1,2-ylenebis(acetic acid) utilizing a functional five-membered heterocycle 4(R)-MCTTThe Journal of Organic Chemistry, 1985
- Enantioselective and Enantioconvergent Syntheses of Building Blocks for the Total Synthesis of Cyclopentanoid Natural ProductsAngewandte Chemie International Edition in English, 1984
- A new nonenzymatic chiral induction into prochiral meso compoundsTetrahedron, 1984
- 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
- A new design for chiral induction: a highly regioselective differentiation between two identical groups in an acyclic compound having a prochiral centerJournal of the American Chemical Society, 1982