Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Thiolated Cinchonidine Quaternary Ammonium Dimers 5
2.2. Synthesis of Cinchonidine Dimers 7 Using Thiol-Ene Click Reaction
2.3. Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers 8 Using Quaternization Polymerization
2.4. Asymmetric Benzylation of N-(Diphenylmethylidene)glycine tert-butyl Ester 9 Catalyzed by Main-Chain Chiral Quaternary Ammonium Polymers 8
Entry | Catalyst | R | Time (h) | Yield (%) a | ee (%) b |
---|---|---|---|---|---|
1 | 5a | 4 | 97 | 84 | |
2 | 5b | 4 | 92 | 90 | |
3 | 5c | 4 | 91 | 88 | |
4 | 5d | 4 | 92 | 90 |
Entry | Catalyst | R1 | R2 | Time (h) | Yield (%) a | ee (%) b |
---|---|---|---|---|---|---|
1 | 8a | 8 | 88 | 86 | ||
2 | 8b | 8 | 84 | 79 | ||
3 | 8c | 8 | 86 | 79 | ||
4 | 8d | 11 | 89 | 87 | ||
5 | 8e | 5 | 53 | 71 | ||
6 | 8f | 8 | 75 | 80 | ||
7 | 8g | 11 | 80 | 88 | ||
8 | 8h | 8 | 85 | 88 |
3. Experimental
3.1. General
3.2. Preparation of Thiolated Chiral Quaternary Ammonium Salt Dimer 5
3.2.1. Preparation of Thiolated Cinchonidine 3
3.2.2. Preparation of Thiolated Chiral Quaternary Ammonium Salt Dimer 5
3.3. Preparation of Main-Chain Chiral Quaternary Ammonium Polymers 8
3.3.1. Preparation of Cinchonidine Dimer 7
3.3.2. Preparation of Main-Chain Chiral Quaternary Ammonium Polymers 8
3.4. General Procedure for Asymmetric Benzylation of N-(Diphenylmethylidene)glycine tert-butyl Ester 9 Catalyzed by Main-Chain Chiral Quaternary Ammonium Polymers 8
4. Conclusions
Acknowledgments
References and Notes
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Haraguchi, N.; Ahamed, P.; Parvez, M.M.; Itsuno, S. Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization. Molecules 2012, 17, 7569-7583. https://doi.org/10.3390/molecules17067569
Haraguchi N, Ahamed P, Parvez MM, Itsuno S. Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization. Molecules. 2012; 17(6):7569-7583. https://doi.org/10.3390/molecules17067569
Chicago/Turabian StyleHaraguchi, Naoki, Parbhej Ahamed, Md. Masud Parvez, and Shinichi Itsuno. 2012. "Synthesis of Main-Chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization" Molecules 17, no. 6: 7569-7583. https://doi.org/10.3390/molecules17067569