The Research On Desymmetrization Of 2-fluorinated-1,3-diols And Its Application

Alcohols are found to be a common organic compounds in nature, acquiring chiral alcohols remains a challenging task among chemists. Among various methods, the desymmetrization of 1,3-diols is an effective method for obtaining chiral diols. To perform such desymmetrization reactions, enzymatic strategy have been traditionally employed as a tool. However, their practical use is often hampered by several limitations as irreproducibility, substrate specificity, availability as a single enantiomeric form, acetyl migration which leads to racemization and high cost among others. Compared with enzymatic methods, desymmetrization of 1,3-diols using metal complexes and small molecule catalysts has emerged as powerful tool which could provide highly enantioenriched compounds. The aforementioned desymmetrization strategy of 1,3-diols to obtain chiral diols can be performed by a simple method which have received widespread attention.In general, the abundance of fluorine element in nature is so high, while at the same time the fluorine containing natural products are rare in nature, and chemists are still eager to prepare more organic compounds containing fluorine atom by using a variety of synthetic methods. The introduction of fluorine atoms into organic compounds have received widespread attention. Because the introduction of fluorine atom into organic compounds will lead to simulation and electronic effect, while at the same time increasing the lipophilicity of organic compounds, which have significant physiological activities. A diverse array of organic compounds such as Casodex, Gemcitabine, etc., have shown exceptional biological profiles because all of them constitute fluoride atom in it. Therefore it is expected to become one of the important members of the synthetic drugs.Moreover enantioselective acylation of alcohols have also been frequently used as an effective method for desymmetrization of 1,3-diols. Comparing with previous report, we reported a highly enantioselective desymmetrization of 2-fluorinated-l, 3-diols has been demonstrated by using chiral phosphoric acids and a series of chiral fluorinated compounds were obtained in high enantioselectivity, the reaction was found to be scalability through gram-scale and found no effect on ee.Furthermore a-Fluorinated-P-amino acids have received widespread attention as building blocks that may endow peptides and proteins with advantageous such as biophysical, chemical and biological properties. Herein we reported the sythesis of a-Fluorinated-β-amino acids obtained from the chiral fluorinated compounds, and finally it can be converted to chiral a-fluorinated-β-aminoalcohol.