Facile access to chiral β-homoglutamic acid from 3-cyclohexene-carboxylic acid

Abstract

A convenient, safe, and effective synthetic protocol for the synthesis of chiral β-homoglutamic acid was described. The strategy started from 3-cyclohexenecarboxylic acid, followed by three steps classic reaction including Curtius Rearrangement, oxidative cleavage of alkene, and debenzylation by catalytic hydrogenation. The chiral β-homoglutamic acid was prepared with a high yield and high enantiomeric excess.

Graphical Abstract

Keywords:

• β-Amino acids
• β-homoglutamic acid
• chiral
• Curtius rearrangement
• 3-cyclohexenecarboxylic acid

Additional information

Funding

The authors gratefully acknowledge financial supports from the Strategic Priority Research Program of the Chinese Academy of Sciences [No. XDB20000000] and the Natural Science Foundation of Fujian Province, China [No. 2018J01029], the Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences.