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Diastereo- and enantioselective catalytic vinylogous mukaiyama-mannich reactions of pyrrole-based silyl dienolates with alkyl-substituted aldehydes

Ranieri, Beatrice and Curti, Claudio and Battistini, Lucia and Sartori, Andrea and Pinna, Luigi and Casiraghi, Giovanni and Zanardi, Franca (2011) Diastereo- and enantioselective catalytic vinylogous mukaiyama-mannich reactions of pyrrole-based silyl dienolates with alkyl-substituted aldehydes. The Journal of Organic Chemistry, Vol. 76 (24), p. 10291-10298. eISSN 1520-6904. Article.

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DOI: 10.1021/jo201875a

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.

Item Type:Article
ID Code:7035
Status:Published
Refereed:Yes
Uncontrolled Keywords:Catalytic Mannich-type reactions, VMMn procedure
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:American Chemical Society
eISSN:1520-6904
Deposited On:30 Jan 2012 13:35

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