Facile access to α,β-dehydroalanine and α,β-dehydroamino butyric acid derivatives from DL-serines and threonines

ABSTRACT

Not only α,β-dehydroamino acids are important constituents for a number of bioactive peptides in nature, but also they are important building blocks for a variety of synthetic amino acids in organic synthesis. Methods to prepare dehydroamino acids have been reported extensively in the literature; however, efficient and convenient protocols are still required. Here we have developed a convenient method to prepare dehydroalanine (ΔAla) and dehydroamino butyric acid (ΔAbu) derivatives derived from DL-serines and DL-threonines, respectively. 4-Toluenesulfonyl chloride (TsCl) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were employed in this procedure, which carried out activation of hydroxyl group and β-elimination in one pot. Because it is convenient and easy to handle, this method will attract the attention of synthetic chemists.

GRAPHICAL ABSTRACT

KEYWORDS:

• Dehydroamino acids
• one pot
• serine
• threonine