title: Diastereo- and enantioselective catalytic vinylogous Mukaiyama-Mannich reactions of pyrrole-based silyl dienolates with alkyl-substituted aldehydes.
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.
authors: Dipartimento Farmaceutico, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy.
authors: Beatrice
authors: B
authors: Ranieri
authors: Claudio
authors: C
authors: Curti
authors: Lucia
authors: L
authors: Battistini
authors: Andrea
authors: A
authors: Sartori
authors: Luigi
authors: L
authors: Pinna
authors: Giovanni
authors: G
authors: Casiraghi
authors: Franca
authors: F
authors: Zanardi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007097:Imines / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001372:Aza Compounds; D001688:Biological Products; D007097:Imines; D007783:Lactones; D011758:Pyrroles; C073080:7-goniofufurone; D012834:Silver