SYNTHESES OF CHIRAL N-SUBSTITUTED MALEIMIDES BEARING TWO POLYMERIZABLE GROUPS

Gao Huajing, Sun Jian, Xie Ning, Jin Zhaohui

ABSTRACT:Chiral (S)-N-maleoyl-L-leucine propargyl ester with a specific rotation of [α]435 = -27.5° and chiral (S)-N-maleoyl-L-leucine allyl ester with a specific rotation of [α]435 = -36.2°, two monomers of N-substituted maleimide (RMI), were successfully synthesized from maleic anhydride, L-leucine, and propargyl alcohol or allyl alcohol accordingly. Both of them simultaneously have an olefinic group of the maleimide moiety and another polymerizable group (double or triple bond) in the ester moiety. 1H NMR, 13C NMR and FT-IR analysis confirmed the structures of them. And their model compounds of (S)-N-succinoyl-L-leucine propargyl ester and chiral (S)-N-succinoyl-L-leucine allyl ester were obtained respectively. The syntheses routes and results of them were reported in detail.

Keywords:Propargyl ester, Allyl ester, N-Substituted maleimide, Synthesis