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.
Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes / Ranieri, Beatrice; Curti, Claudio; Battistini, Lucia; Sartori, Andrea; Pinna, L.; Casiraghi, Giovanni; Zanardi, Franca. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 76:(2011), pp. 10291-10298. [10.1021/jo201875a]
Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes
RANIERI, Beatrice;CURTI, Claudio;BATTISTINI, Lucia;SARTORI, Andrea;CASIRAGHI, Giovanni;ZANARDI, Franca
2011-01-01
Abstract
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.File | Dimensione | Formato | |
---|---|---|---|
n59_abst.pdf
non disponibili
Tipologia:
Abstract
Licenza:
Creative commons
Dimensione
167.54 kB
Formato
Adobe PDF
|
167.54 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.