Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding
| Autor: | Roderick W. Bates, Bao Nguyen Do Doan, Vasudeva Rao Gandi, Sivarajan Kasinathan |
|---|---|
| Přispěvatelé: | School of Physical and Mathematical Sciences |
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_element
Ligand Chemistry Techniques Synthetic 010402 general chemistry Ligands 01 natural sciences Biochemistry Catalysis Rhodium chemistry.chemical_compound Chemistry [Science] Moiety Hydroxymethyl Physical and Theoretical Chemistry Amino Acids Pipecolic acid 010405 organic chemistry Hydrogen bond Organic Chemistry Hydrogen Bonding Stereoisomerism Combinatorial chemistry 0104 chemical sciences Lincomycin chemistry Hydrogenation Phosphine Hydrogen |
| Zdroj: | Organicbiomolecular chemistry. 17(10) |
| ISSN: | 1477-0539 |
| Popis: | A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding. ASTAR (Agency for Sci., Tech. and Research, S’pore) Accepted version |
| Databáze: | OpenAIRE |
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