A domino reaction of a β-ketoester, phenylethylamine and ethyl glyoxylate: leading to chiral tricarboxylate containing multiple stereocenters

A new type of chiral tricarboxylate containing multiple stereocenters was synthesized via the one-pot reaction of a β-ketoester, (S)-phenylethylamine, and ethyl glyoxylate. High yields and diastereoselectivities (up to 96:4 dr) were obtained under optimal conditions. The reaction of the chiral tricarboxylate with Zn(BH4)2 gave chiral γ-lactones in good yields with up to 92:8 dr. The structures and configurations of the new chiral tricarboxylates were characterized by X-ray diffraction analysis.

Graphical abstractA new type of chiral tricarboxylate containing multiple stereocenters was synthesized via the one-pot reaction of β-ketoester, (S)-phenylethylamine, and ethyl glyoxylate under very mild reaction conditions. The reaction of compound 2 with Zn(BH4)2 provides γ-lactone 7 up to 92:8 dr.Figure optionsDownload full-size imageDownload as PowerPoint slide