Facile access to α, β-dehydroalanine and α, β-dehydroamino butyric acid derivatives from DL-serines and threonines. Issue 11 (2nd June 2016)

• Record Type: Journal Article
• Authors: Yang, Yong-Qing; Ji, Meng-Chen; Lu, Zheng; Jiang, Mao; Huang, Wei-Wei; He, Xue-Zhi
• Is Part Of: Synthetic communications. Volume 46:Issue 11(2016)
• Page Start: 977
• Page End: 982
• Publication Date: 2016-06-02
• Subjects: Dehydroamino acids -- one pot -- serine -- threonine; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2016.1149194
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: Not onlyα, 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 andβ -elimination in one pot. Because it is convenient and easy to handle, this method will attract the attention of synthetic chemists. GRAPHICAL ABSTRACT: