1350461-49-2Relevant academic research and scientific papers
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, Luigi,Casiraghi, Giovanni,Zanardi, Franca
supporting information; scheme or table, p. 10291 - 10298 (2012/02/13)
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 (Figure presented).
