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首页> 外文期刊>Journal of Applied Polymer Science >Thermo-responsive block copolymermicelle-supported(S)-alpha,alpha-diphenylprolinoltrimethylsilyl ether for asymmetric Michael addition of nitroalkenes and aldehydes in water
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Thermo-responsive block copolymermicelle-supported(S)-alpha,alpha-diphenylprolinoltrimethylsilyl ether for asymmetric Michael addition of nitroalkenes and aldehydes in water

机译：热响应嵌段共聚物支持（S） - alpha，α-二苯基脯氨酸三甲基甲硅烷基醚，用于不对称Michael加入水中的Nitroallenes和醛

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摘要

An amphiphilic block copolymer PNIPAM(53)-b-(PS30-co-P4AMS(10)) was facilely prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. The immobilization of (S)-alpha,alpha-diphenylprolinol trimethylsilyl ether onto the block copolymers was then performed through using copper-catalyzed alkyne-azide cycloaddition (CuAAC), and the generating amphiphilic diblock copolymer supported chiral catalyst PNIPAM(53)-b-(PS30-co-P4AMS(10))/proTMS was self-assembled into micelles with regular diameters about 50 nm in aqueous solution. The micellar catalyst was further used for the asymmetric Michael reaction between propanal andtrans-beta-nitrostyrene in water. Using only 1 mol% micellar catalyst, the corresponding Michael addition products could be obtained in good yields and high enantioselectivities as well as good diastereoselectivities. In addition, this micellar catalyst could be reused at least for four times. Moreover, the micellar catalyst could be applied for the asymmetric addition reaction of 4-chlorocinnamyl aldehyde and nitromethane, and thus constructing the baclofen pharmaceutical intermediate.
机译：采用可逆加成-断裂链转移（RAFT）聚合方法制备了两亲性嵌段共聚物PNIPAM（53）-b-（PS30-co-P4AMS（10））。然后，通过使用铜催化的炔叠氮环加成（CuAAC）将（S）-α，α-二苯基脯氨酸三甲基硅基醚固定在嵌段共聚物上，并且生成的两亲性二嵌段共聚物负载的手性催化剂PNIPAM（53）-b-（PS30-co-P4AMS（10））/proTMS在水溶液中自组装成直径约为50nm的规则胶束。胶束催化剂进一步用于丙醛和反式β-硝基苯乙烯在水中的不对称Michael反应。仅使用1mol%的胶束催化剂，即可获得产率高、对映选择性高、非对映选择性好的Michael加成产物。此外，这种胶束催化剂至少可以重复使用四次。此外，胶束催化剂可用于4-氯肉桂醛与硝基甲烷的不对称加成反应，从而构建巴氯芬医药中间体。

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