Asymmetric Synthesis of Chiral Dinitro- and Trinitroazetidine Derivatives
Nitroazetidine derivatives, such as 3,3-dinitroazetidine (DNAZ), 1,3,3-trinitroazetidine (TNAZ), N-2',4'-dinitrophenyl-3,3-dinitroazetidine (DNPDNAZ) and 1-nitroso-3,3-dinitroazetidine (nitroso-DNAZ), are important materials having high energies resulting from the highly strained azetidine ring and the nitro groups. In addition, 1-bromoacetyl-3,3-dinitroazetidine (ABDNAZ) as one of the energetic nitroazetidine derivatives has recently been developed as anticancer agent and radiation sensitizer in pharmaceutical research field. Because of these importances, considerable effort has been devoted to the development of a variety of nitroazetidine derivatives. Recently, the C-subsitituted-TNAZs have been synthesized in our laboratory.
As a further development of new synthetic routes to a variety of chiral nitroazetidines, I present the asymmetric synthesis of 2-nitratoethyl-TNAZ, 2-nitratoethyl-3-methylnitrato-1,3-dinitroazetidine (2-nitratoethyl-NMDNAZ) and dimeric-TNAZ.