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Volumn , Issue 2, 2007, Pages 255-258

Naturally occurring α-amino acid catalyzed coupling of carbon dioxide with epoxides to afford cyclic carbonates

Author keywords

Amino acids; Carbon dioxide; Coupling reaction; Cyclic carbonates; Epoxides

Indexed keywords

ALPHA AMINO ACID; AMMONIA; CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID; EPOXIDE; PHENYLALANINE;

EID: 33847042273     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968024     Document Type: Article
Times cited : (39)

References (40)
  • 1
    • 0035323783 scopus 로고    scopus 로고
    • Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; Dubois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.;Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953.
    • (a) Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; Dubois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.;Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953.
  • 30
    • 33847073751 scopus 로고    scopus 로고
    • Typical Experimental Procedure: Propylene oxide (20 mmol, L-phenylalanine (0.16 mmol) and CH2Cl2 (1 mL) were added into a 15 mL stainless autoclave with a magnetic stirrer, and CO 2 (liquid, 3.2 MPa) was charged into the reactor at r.t. The initial pressure was generally adjusted to 6 MPa at 130°C. The autoclave was heated at that temperature for 48 h, and the pressure was kept constant during the reaction. After the reaction, the reactor was cooled to 0°C, and extra CO2 was vented slowly. The crude product was analyzed by a gas chromatograph, compared with authentic sample, and the yields were determined by GC using tridecane as internal standard. The crude product (yield: 100% by GC) was purified by distillation and propylene carbonate was obtained in 93% isolated yield. The cyclic carbonate was identified by IR, GC/MS (HP6890/ 5973) and 400 MHz NMR spectroscopy
    • 2 was vented slowly. The crude product was analyzed by a gas chromatograph, compared with authentic sample, and the yields were determined by GC using tridecane as internal standard. The crude product (yield: 100% by GC) was purified by distillation and propylene carbonate was obtained in 93% isolated yield. The cyclic carbonate was identified by IR, GC/MS (HP6890/ 5973) and 400 MHz NMR spectroscopy.
  • 31
    • 33847029541 scopus 로고    scopus 로고
    • Spectroscopic data of the cyclic carbonates: 4-Methyl-1,3-dioxolan-2- one(2a, IR (neat, 1795 (C=O) cm-1. MS (EI, m/z, 102 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 1.48 (d, J, 3.6 Hz, 3 H, CH3, 4.01 (t, J, 8.4 Hz, 1 H, CH, 4.53 (t, J, 8.0 Hz, 1 H, CH, 4.81-4.86 (m, 1 H, CH, 4-Chloromethyl-1,3-dioxolan-2-one(2b, IR (neat, 1790 (C=O) cm -1. MS (EI, m/z, 136 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 3.72-3.74 (m, 2 H, CH2, 4.38 (q, J, 6.0 Hz, 1 H, CH, 4.57 (t, J, 8.4 Hz, 1 H, CH, 4.91-1.94 (m, 1 H, CH, 4-Phenyl-1,3-dioxolan-2-one (2c, IR (neat, 1816 (C=O) cm-1. MS (EI, m/z, 164 [M, 1H NMR (400 MHz, TMS, CDCl3, δ, 4.31-4.35 (m, 1 H, CH, 4.76-4.82 (m, 1 H, CH, 5.66 (t, J, 8.0 Hz, 1 H, CH, 7.32-7.44 m, 5 H, C
    • 2), 4.63-4.68 (m, 2 H, CH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.