Diastereoselective access to trans-2-substituted cyclopentylamines
| Autor: | Antoine Joosten, Jan Szymoniak, Emilie Lambert, Jean-Luc Vasse |
|---|---|
| Přispěvatelé: | Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2010 |
| Předmět: |
Tandem
Molecular Structure 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Stereoisomerism Cyclopentanes 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Cyclization Molecule [CHIM]Chemical Sciences Anilides Physical and Theoretical Chemistry Amines Oxazoles Sequence (medicine) Lewis Acids |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2010, 12 (22), pp.5128-5131. ⟨10.1021/ol102038x⟩ |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol102038x⟩ |
| Popis: | International audience; A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely substituted cyclopentylamines which appear to be useful synthetic intermediates. This was further illustrated by the syntheses of (±)-Rodocaine, (±)-trans-pentacin, and enantiomerically enriched trans-cyclopentane-1,2-diamine. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|