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Thermo‐responsive block copolymer micelle‐supported ( S )‐α, α‐diphenylprolinol trimethylsilyl ether for asymmetric Michael addition of nitroalkenes and aldehydes in water
Author(s) -
Li Tao,
Wang Weilin,
Wang Songmeng,
Liu Lingyan,
Chang Weixing,
Li Jing
Publication year - 2021
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.49831
Subject(s) - copolymer , polymer chemistry , micelle , amphiphile , catalysis , chemistry , ether , chain transfer , michael reaction , organic chemistry , aqueous solution , radical polymerization , polymer
An amphiphilic block copolymer PNIPAM 53 ‐ b ‐(PS 30 ‐ co ‐P4AMS 10 ) was facilely prepared by reversible addition‐fragmentation chain transfer (RAFT) polymerization. The immobilization of ( S )‐α,α‐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 ‐(PS 30 ‐ 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 and trans ‐β‐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.