Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C2-symmetric chiral template.
نویسندگان
چکیده
A chiral template was constructed from 7-ethynyl-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one by Sonogashira cross-coupling with 4,4''-diiodoterphenyl and was shown to bind the title compound strongly by hydrogen bonding resulting in enantioselectivities of up to 55% enantiomeric excess (ee) in the [4+4] anthracene photodimerization.
منابع مشابه
Synthesis and crystal structure compound Adeninium Bis(pyridine-2,6-dicarboxylate) Chromate(III) pyridine-2,6-dicarboxylic acid tetra hydrate
A new supramolecular compound of adeninium bis(pyridine-2,6-dicarboxylate) Chromate(III) pyridine-2,6-dicarboxylic acid tetrahydrate (AdH+)[Cr(pydc)2](H2pydc).4H2O (1) (where Ad and H2pydc are adenine and pyridine-2,6-dicarboxylic acid, respectively) was synthesized via proton transfer method and its structure was determined using single crystal X-ray diffraction technique. This compound crysta...
متن کاملSynthesis and characterization of some new C2 symmetric chiral bisamide ligands derived from chiral Feist's acid.
The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5(a-d) and (1S,2S)-6(a-d) were synthesized in quantitative yield from (1R,2R)-(+)-3-methylenecyclo-propane-1,2-dicarboxylic acid (1R,2R)-3 and (1S,2S)-(-)-3-methylene-cyclopropane-1,2-dicarboxylic acid (1S,2S)-3, in two steps, respectively. The chiral Feist's acids (1R,2R)-3 and (1S,2S)-3 were obtained in good isom...
متن کاملExpanding the registry of aromatic amide foldamers: folding, photochemistry and assembly using diaza-anthracene units.
The synthesis of various 1,8-diaza-4,5-dialkoxy-2,7-anthracene dicarboxylic acid derivatives and their incorporation into cyclic and helically folded aromatic oligoamides are reported. The ability of the diaza-anthracene monomers to undergo photoaddition or head-to-tail photodimerization was investigated in the solid state and in solution. Quantitative conversion of a monomer diester to the cor...
متن کاملChiral multidentate oxazoline ligands based on cyclophosphazene cores: synthesis, characterization and complexation studies.
Chiral oxazoline based bi and hexadentate ligands built on cyclophosphazene cores have been synthesized and characterized. (NPPh2)2[NP(m-OC6H4C(O)OCH3)2] (1) was prepared by the reaction of gem-(NPPh2)2(NPCl2) with methyl-3-hydroxy benzoate in the presence of Cs2CO3. Compound 1 was converted to the dicarboxylic acid (NPPh2)2[NP(m-OC6H4C(O)OH)2] (2) by base promoted hydrolysis with KO(t-Bu). The...
متن کاملEnantioselective Synthesis of Modafinil Drug using Chiral Complex of Titanium and Diethyltartarate
Modafinil (Diphenyl methyl Sulfinyl acetamid) is used clinically in the treatment of narcolepsy and sleeping disorders. The synthesis of R-modafinil, have started with the reaction of benzhydrol and thioglycolic acid in trifluoroacetic acid to afford benzhydryl sulfanyl acetic acid. The reaction of acid with thionyl chloride in benzene followed by treatment with ammonium hydroxide gave acetamid...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 52 5 شماره
صفحات -
تاریخ انتشار 2016