Synthesis And Catalytic Research By Chiral BINOL Phosphoric Acids Complexes

Chiral asymmetric organocatalysis has the advantage of environmentally friendly and it can be synthesized and preserved easily, which is the asymmetric catalysts’s direction in future development. As one of Br(?)nsted acids, chiral phosphoric acid is developing rapidly and attracts high attention of people within ten years.The main content of this thesis is to synthesis15kinds of phosphoric acid catalysts from chiral BINOL with inexpensive2-naphtol by optimizing reaction routes, and these catalysts were applied to the asymmetric Friedel-Crafts reaction.Chapter1Introduction. There are four parts in this section:(1) The development and background in chiral asymmetric organocatalysis;(2) The research in phosphoric acid catalysts and asymmetric reaction type of catalyze at home and abroad;(3) Simply introduced the catalytic mechanism;(4) The aim and significance of the research in this thesis.Chapter2This section was the hardcore of the research in this thesis. Chiral BINOL is synthesized with2-naphthol and4different groups were added in3-bit,3’-bit,3,3’-bit and6,6’-bit of chiral BINOL, including4-isopropyl phenyl,2-nitrophenyl,2,4,6-three isopropyl phenyl. At last,15kinds of catalysts were synthesized by Li-X exchange reaction, Suzuki coupled reaction, Kumada coupled reaction and Sonogashira reaction.Chapter3Parts of the catalysts were used in asymmetric Friedel-Crafts reaction of Boc-3phenyl-enamine and indole. Solvent, Catalytic, temperature and time, and selection and dosage of catalyst were changed for studying the catalytic performance of different catalysts. At last, we got69%yield and84%ee.Chapter4Synthesis of Azaallyl ligands and its metal compounds from o-toluidine and acetophenone by several steps.