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Asymmetric Polymerizations of N-Substituted Maleimides Bearing L-Leucine Ester Derivatives and Chiral Recognition Abilities of Their Polymers

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Asymmetric Polymerizations of N-Substituted Maleimides Bearing L-Leucine Ester Derivatives and Chiral Recognition Abilities of Their Polymers Polymer Journal, Vol. 39, No. 10, pp. 1047–1059 (2007) #2007 The Society of Polymer Science, Japan Asymmetric Polymerizations of N-Substituted Maleimides Bearing L-Leucine Ester Derivatives and Chiral Recognition Abilities of Their Polymers y Tsutomu OISHI, Huajing GAO, Taro NAKAMURA, Yukio ISOBE, and Kenjiro ONIMURA Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube 755-8611, Japan (Received April 27, 2007; Accepted July 8, 2007; Published August 28, 2007) ABSTRACT: Two kinds of N-substituted maleimides bearing L-leucine ester derivatives ((S)-RLMI), i.e. (S)-N- maleoyl-L-leucine methyl ester ((S)-MLMI) and (S)-N-maleoyl-L-leucine benzyl ester ((S)-BnLMI), were synthesized from maleic anhydride, L-leucine, and corresponding alcohols. Asymmetric polymerizations were carried out to obtain optically active polymers. Specific rotations of the poly (RLMI)s were influenced by N-substituents, initiators, solvents and temperature. Chiroptical properties and structures of the poly((S)-RLMI)s obtained were investigated by GPC, CD, and NMR measurements. Optical activities of the poly((S)-RLMI)s obtained with anionic polymerization were attrib- uted to excessive chiral centers of the main chain induced through the polymerizations in addition to the chirality of the N-substituents. The chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC) were prepared and the chiral recognition abilities of the optically active poly((S)-RLMI)s were also discussed. [doi:10.1295/polymj.PJ2007022] KEY WORDS Maleimide / Chiral Recognition Ability / Leucine / Optically Active Polymer / Asymmetric Polymerization / Chiroptical Properties / Chiral Stationary Phase / The synthesis of optically active polymer is an im- chiral N-substituted maleimides (RMIs) to obtain op- portant field in macromolecular science because of a tically active polymers and optical resolution abilities wide variety of potential applications based on the of the poly(RMI)s obtained.11–33 In 1991, Oishi et al. chiral structure, such as constructing chiral media reported their first research on asymmetric anionic for asymmetric synthesis; chiral stationary phases polymerizations of eleven types of achiral RMIs (N- for resolution of enantiomers in chromatographic substitutent (R) = n-propyl (PMI), isopropyl (IPMI), techniques; chiral liquid crystals in ferroelectrics and n-butyl (NBMI), isobutyl (IBMI), s-butyl (SBMI), nonlinear optical devices.1–4 Therein, the stationary t-butyl (TBMI), cyclohexyl (CHMI), benzyl (BZMI), phase for chiral high-performance-liquid-chromatog- phenyl (PhMI), 1-naphthyl (1-NMI), and 2-fluorenyl raphy separation is one of the most successful applica- (FMI)) with n-BuLi/(À)-Sparteine (Sp) complex as tions of optically active polymers.5–8 Thus, great at- initiator.12 In these poly(RMI)s, poly(CHMI) showed 25 tentions are paid to the syntheses of optically active the highest specific rotation (½ D = ca. À40 ). polymers capable of chiral recognition. Achiral N-glycinylmaleimide (GMI) and N-substitut- According to the previous researches,9,10 optically ed maleimide having glycine ester derivative from active polymers are synthesized either by the poly- glycine (achiral amino acid) have also been synthe- merization of monomers having an optically active sized and their polymers have not been found showing moiety without chiral induction to the polymer chain chiral recognition abilities.31,32 Besides the above re- or by polymerization in which chirality is introduced searches on achiral RMIs, asymmetric polymeriza- into the polymer structure through the asymmetric tions of chiral RMIs bearing chiral amine, such as (R)- polymerization reaction. Chiral induction can be N- -methylbenzylmaleimide ((R)-(À)-MBZMI),20 achieved either by catalytic reaction by using achiral (S)-N- -methylbenzylmaleimide ((S)-(À)-MBZMI),21 or chiral monomers or by non-catalytic reaction sys- (S)-N-1-cyclohexylethylmaleimide ((S)-CEMI),28 (R)- tems typically based on chiral monomer structure. N-1-cyclohexylethylmaleimide ((R)-CEMI),28 and As one of useful methods, asymmetric synthesis poly- (S)-N-1-naphthylethylmaleimide ((S)-NEMI)33 were merization can produce the polymers with configura- also carried out, and polymers with higher specific tional chirality of the main chain from an optically in- rotations were obtained. Chiral RMIs are being ex- active, prochiral monomer or a prochiral monomer pected to provide high optically active polymers be- bearing an optically active auxiliary. cause of their new chiralities of main chains in addi- In the past decades, Oishi et al. have systematically tion to the chiralities of N-substituents. Amino acids researched asymmetric polymerizations of achiral or are important and useful substances for chiral auxilia- yTo whom correspondence should be addressed (Tel: +81-836-85-9281, Fax: +81-836-85-9201, E-mail: [email protected]). 1047 T. OISHI et al. NH2 NH2 HCl NH2 OH SOCl2 O Et3N in EtOAc O * * * O in MeOH O O L-Leucine (S )-Leucine methyl ester NH 1) ZnBr , 50oC 2 O O O O 2 O O N O O NH OH * 2) HMDS, 80oC in EtOAc O O O * 3) reflux, 12 h * O O (S )-MLMA (S)-MLMI Scheme 1. Synthesis of (S)-MLMI ries and building blocks in organic syntheses.34,35 the CSPs prepared from the polymers are carried out. Because the varieties of chiral amino acids are very Chiral recognition abilities of the polymers are dis- abundance, we can design some new chiral RMIs by cussed. introducing expected chiral amino acid to the N-sub- stituent of maleimide and other various substituents EXPERIMENTAL are introduced to the carboxyl group of the side amino acid group in the RMI. From this point of view, Oishi Reagents et al. have chosen some chiral amino acids, such as Solvents used for syntheses, polymerizations, and L-alanine, L-phenylalanine, L-valine, D-phenylglycine measurements were purified in the usual manner. and so on, as experimental subjects and reported the Commercially available n-butyllithium (n-BuLi) syntheses and asymmetric polymerizations of N-male- (Kanto Chemical Co., Inc., in n-hexane solution, 14,15 oyl-L-phenylalanine alkyl ester, N-maleoyl-L-ala- 1.55 mol/L), dimethylzinc (Me2Zn) (Kanto Chemical nine ester (RAM),16 chiral (S)-N-maleoyl-L-valine Co., in n-hexane solution, 1.00 mol/L) were used 27 methyl ester ((S)-MVMI), chiral (R)-N-maleoyl-D- without further purification. Diethylzinc (Et2Zn) was phenylglycine alkyl ester.29 At the same time, the re- kindly supplied from Tosoh Corporation, and diluted searches have also been reported about the applica- with purified n-hexane (0.82 mol/L). (À)-Sparteine tions of poly(RMI)s on optical resolutions of race- (Sp) (Tokyo Chemical Industry Co., Ltd.) was used mates by being used as CSPs for HPLC.29,33,36 after purification by distillation under reduced pressure Several racemates were resolved by the CSPs pre- (½ 435 ¼À10:3 (c ¼ 1:0 g/dL, l ¼ 10 cm, THF)). pared from the corresponding polymers. (S,S)-(1-Ethylpropylidene)bis(4-benzyl-2-oxazoline) Very recently, we have published the asymmetric (Bnbox, ½ 435 ¼À150:7 (c ¼ 1:0 g/dL, l ¼ 10 cm, polymerizations of (S)-N-maleoyl-L-leucine propargyl THF)) was prepared according to the published litera- ester37,38 and (S)-N-maleoyl-L-leucine allyl ester,39 ture.40 Radical initiator, 2,20-azobisisobutyronitrile both of which having an unsaturated reactive group (AIBN) (Ishizu Seiyaku, Ltd.) was purified by recrys- in the side ester group of RMI. The optical resolutions tallization from methanol. Palladium-activated carbon of the chemically bonded-type chiral stationary phases (Wako Pure Chemical Industries, Ltd., Pd 10%) was (CSPs) using their polymers were also discussed. This used as purchased. Microporous silica gel (Si-100, time, we choose L-leucine as chiral amino acid and re- pore size 100 A˚ , mean particle size 5 mm) and race- spectively introduce methyl group and benzyl group mates were kindly supplied from Tosoh Corporation to the carboxyl group of L-leucine to extend our re- and used without further purification. search width. In this work, we describe syntheses and asymmetric polymerizations of (S)-N-maleoyl-L- Synthesis of Monomer ((S)-MLMI) leucine methyl ester ((S)-MLMI) and (S)-N-maleoyl- Synthetic route of (S)-MLMI is shown in L-leucine benzyl ester ((S)-BnLMI)—other two kinds Scheme 1. Thionyl chloride (SOCl2) (39.8 mL, 0.55 of RMIs bearing L-leucine ester derivatives, and the mol) was added dropwise to methanol (MeOH) applications of theirs polymers as CSPs for HPLC. (200 mL) in a three-neck flask at À10 C. Then L-leu- Chiroptical properties and structures of these poly- cine (20.0 g, 0.15 mol) was added slowly to this solu- mers were investigated in detail on the basis of meas- tion at the same temperature. The mixture was stirred urements of nuclear magnetic resonance (NMR), spe- for 15 h at room temperature. After reaction, methanol cific optical rotations, circular dichroism (CD), and and excess thionyl chloride were removed by distilla- gel permeation chromatography (GPC). Furthermore, tion under reduced pressure. The residue was crystal- the HPLC analyses for separations of racemates using lized from diethyl ether. After filtered and dried under 1048 Polym. J., Vol. 39, No. 10, 2007 Asymmetric Polymerizations of RLMI vacuum, (S)-leucine methyl ester hydrochloride was H2, Pd/C obtained as a white powder [yield: 27.0 g (97.5%)]. O N O O N O (S)-Leucine methyl ester hydrochloride (10.0 g, O in EtOAc at r.t. O 55.0 mol) was suspended into ethyl acetate (EtOAc) * * O O (100 mL). Triethylamine (Et3N) (6.8 mL, 48.3 mol), (S )-MLSI which was dissolved in ethyl acetate (50 mL), was (S )-MLMI dropwise added into the mixture. After stirred over Scheme 2. Synthesis of (S)-MLSI 10 minutes, it was collected by suction filtration. Maleic anhydride (5.4 g, 55.0 mol) was dissolved into ethyl acetate (50 mL), and then added into the above by an aspirator and replaced by nitrogen gas.
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