Abstract
Tetrasubstituted pyrrolidines representing analogs of homoproline were synthesized by three-component condensation of aryl(heteroaryl)aldehydes, asparagine and N-methylmaleimide (NMM). Compounds with (1S*, 3R*, 3aS*, 6aR*)-configuration at the corresponding carbon positions of the bicyclic pyrrolidine ring could be isolated on a preparative scale.
Highlights
Introduction βAmino acids receive considerable interest due to their biologically important properties, their occurrence in natural products, and as potential precursors for β-lactams
To access a diversity of synthesized “homoprolines” 1 we have studied trapping of 1,3-azomethine ylide 2 produced by a decarboxylative route with dipolarophiles (NMM in Molecules 2005, 10 our study, Scheme 1)
1,3-Dipolar cycloaddition of dipolarophiles to azomethine ylides generated from the corresponding imines is a widely used method of pyrrolidine synthesis [9]
Summary
Introduction βAmino acids receive considerable interest due to their biologically important properties, their occurrence in natural products, and as potential precursors for β-lactams. Retrosynthetic scheme of homoproline 1 synthesis by consequent decarboxylative 1,3-dipole generation – cycloaddition 1,3-Dipolar cycloaddition of dipolarophiles to azomethine ylides generated from the corresponding imines is a widely used method of pyrrolidine synthesis [9]. If aspartic acid or asparagine (3) is used as amino acid component in this approach the formation of homoproline 1 could be predicted.
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