Asymmetric Synthesis. XVIII. Stereocontrolled Synthesis of α-Substituted-2-furfurylamines via Chiral Intermediates
- 1 September 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (17) , 2485-2488
- https://doi.org/10.1080/00397919308011135
Abstract
The stereocontrolled synthesis of (R)-α-alkyl-2-fur furylamines (5), using (-)-2-hydroxypinan-3-one (1) as a chiral auxiliary, had been studied. The e. e values of (5) were 91.4->98%, which determined by capillary GC (stationary phase: Chirasil-Val).Keywords
This publication has 10 references indexed in Scilit:
- Asymmetric Synthesis XV: Enantioselective Syntheses of (R) or (S) —α—Substituted— (2 — Pyridyl) Methylamines Via Chiral Pinanone Ketimine TemplateSynthetic Communications, 1991
- Asymmetric Synthesis XI: Stereoselective Synthesis of α-Alkyl-2-Furfurylamines Via d-Camphor Ketimine IntermediateSynthetic Communications, 1990
- A New Synthesis of O-Benzyl-L-ThreonineSynthetic Communications, 1989
- 1,2-Dihydroisoindolines from Intramolecular [4+2] Cycloaddition of N-Allyl-2-Furfurylamine HalohydratesSynthetic Communications, 1988
- Chemoenzymic synthesis of chiral furan derivatives: useful building blocks for optically active structuresThe Journal of Organic Chemistry, 1988
- The aza-achmatowicz rearrangement: A route to useful building blocks for N- containing structuresTetrahedron Letters, 1986
- Cyclodextrin catalysis in the intramolecular Diels-Alder reaction with the furan dieneJournal of the American Chemical Society, 1982
- THE ASYMMETRIC DIELS–ALDER REACTIONS OF α,β-UNSATURATED CARBOXYLIC AMIDES DERIVED FROM (−)-PHENYLGLYCINOL AND THE ASYMMETRIC TOTAL SYNTHESIS OF (+)-FARNESIFEROL CChemistry Letters, 1981
- Diels-Alder Reaction of Furfurylamine Derivatives with Maleic Anhydride and Its StereochemistryYAKUGAKU ZASSHI, 1980
- Synthesis and stereochemistry of the four isomeric pinane-2,3-diolsThe Journal of Organic Chemistry, 1971