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

作者：Huang, Xiaoguang; Chen, Xueming; Chen, Yunyun; Zhang, Aiqin; Li, Xingshu^*

来源：Tetrahedron: Asymmetry , 2008, 19(21): 2529-2535.

DOI：10.1016/j.tetasy.2008.10.028

A new type of chiral tricarboxylate containing multiple stereocenters was synthesized via the one-pot reaction of a beta-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 gamma-lactones in good yields With Lip to 92:8 dr. The structures and configurations of the new chiral tricarboxylates were characterized by X-ray diffraction analysis.

• 出版日期2008-11-3
• 单位中山大学