Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives
| Autor: | Matthew J. Durbin, Angela J. Russell, Stephen G. Davies, Scott J.S. Hartman, Andrew D. Smith, Paul M. Roberts, Ai Matsuno, Steven M. Toms, James E. Thomson |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
Tert butyl
chemistry.chemical_classification Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Medicinal chemistry Catalysis Kinetic resolution Inorganic Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Amide Lithium Physical and Theoretical Chemistry Ene reaction Alkyl |
| Zdroj: | Tetrahedron: Asymmetry. 19:2870-2881 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2008.11.019 |
| Popis: | Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl-N-(α-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. © 2008 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect