Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes
| Autor: | Giovanni Casiraghi, Andrea Sartori, Lucia Battistini, Beatrice Ranieri, Claudio Curti, Luigi Pinna, Franca Zanardi |
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| Rok vydání: | 2011 |
| Předmět: |
Silver
Silylation Chemistry Techniques Synthetic Catalysis Lactones chemistry.chemical_compound Organic chemistry Pyrroles heterocyclic compounds Amino Acids Alkyl Pyrrole chemistry.chemical_classification Aldehydes Aza Compounds Biological Products Molecular Structure Organic Chemistry Chiral ligand Enantioselective synthesis Stereoisomerism Amino acid chemistry Imines Chirality (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 76:10291-10298 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo201875a |
| Popis: | A reliable, catalytic asymmetric vinylogous Mukaiyama-Mannich reaction of pyrrole-based silyl dienolates is introduced that is particularly apt for alkyl- and α-alkoxyalkyl-substituted aldehydes. The reaction course is effectively orchestrated by the Hoveyda-Snapper amino acid-based chiral ligand/silver(I) catalyst combination to produce valuable vicinal diamino carbonyl compounds in high yields, with virtually complete γ-site- and anti-selectivity and significant catalyst-to-product chirality transfer. The utility of the Mannich products can be seen in the synthesis of an unprecedented perhydrofuro[3,2-b]pyrrolone product, an aza-analogue of naturally occurring (+)-goniofufurone. |
| Databáze: | OpenAIRE |
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