Enantiomerically Pure α-Amino Acid Synthesis via Hydroboration−Suzuki Cross-Coupling
| Autor: | Richard J. K. Taylor, Andrew D. Campbell, Ian Patel, Tony M. Raynham, Philip N. Collier |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy Molecular Structure Bromates Alkene Vinyl bromide Aryl Organic Chemistry Chemistry Organic Stereoisomerism Catalysis Amino acid chemistry.chemical_compound Hydroboration chemistry Suzuki reaction Functional group Organic chemistry Chromatography Thin Layer Amino Acids Methylene Palladium |
| Zdroj: | The Journal of Organic Chemistry. 67:1802-1815 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo010865a |
| Popis: | The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis−oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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