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Volumn 72, Issue 20, 2007, Pages 7567-7573

Totally selective reaction of CO2 with enantiopure amino epoxides under mild reaction conditions. Synthesis and synthetic applications of enantiopure (4R, 1′S)- or (4S,1′S)-4-(1-aminoalkyl)-2-oxo-1,3- dioxolanes

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; EPOXY RESINS; HYDROLYSIS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34848873725     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070829x     Document Type: Article
Times cited : (10)

References (64)
  • 7
    • 0001409011 scopus 로고    scopus 로고
    • (g) Gibson, D. H. Chem. Rev. 1996, 96, 2063-2096.
    • (1996) Chem. Rev , vol.96 , pp. 2063-2096
    • Gibson, D.H.1
  • 12
    • 0037454053 scopus 로고    scopus 로고
    • To see a review of the synthetic applications of cyclic carbonates: Clements, J. H. Ind. Eng. Chem. Res. 2003, 42, 663-674.
    • To see a review of the synthetic applications of cyclic carbonates: Clements, J. H. Ind. Eng. Chem. Res. 2003, 42, 663-674.
  • 19
    • 34848924153 scopus 로고    scopus 로고
    • U.S. Pat 5.098.594, 1992; Chem. Abstr. 1992, 112, 121161t
    • (a) Duscher, P. A.; Whash, K. U.S. Pat 5.098.594, 1992; Chem. Abstr. 1992, 112, 121161t.
    • Duscher, P.A.1    Whash, K.2
  • 20
    • 34848905490 scopus 로고    scopus 로고
    • U.S. Pat 5.007.969, 1991; Chem. Abstr. 1992, 112, 121161t
    • (b) Duscher, P. A.; Whash, K. U.S. Pat 5.007.969, 1991; Chem. Abstr. 1992, 112, 121161t.
    • Duscher, P.A.1    Whash, K.2
  • 21
    • 34848849645 scopus 로고    scopus 로고
    • U.S. Pat 5.204.026, 1993; Chem. Abstr. 1993, 119, 98532y
    • (c) Duscher, P. A. U.S. Pat 5.204.026, 1993; Chem. Abstr. 1993, 119, 98532y.
    • Duscher, P.A.1
  • 30
    • 0035944463 scopus 로고    scopus 로고
    • and references cited therein
    • (f) George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393-10394 and references cited therein,
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 10393-10394
    • George, M.1    Weiss, R.G.2
  • 41
    • 33947224600 scopus 로고    scopus 로고
    • 2 with epoxides without the use of a metal catalyst: (a) Jagtap, S. R.; Raje, V. P.; Samant, S. D.; Bhanage, B. M. J. Mol. Catal. A: Chem. 2007, 266, 69-74.
    • 2 with epoxides without the use of a metal catalyst: (a) Jagtap, S. R.; Raje, V. P.; Samant, S. D.; Bhanage, B. M. J. Mol. Catal. A: Chem. 2007, 266, 69-74.
  • 51
    • 34848821772 scopus 로고    scopus 로고
    • 1. Absolute structure was checked using Friedel pairs and chemical information. CCDC-630533 (3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/conts/retrieving.html (or the Cambridge Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336.033; or deposit@ccdc.cam.ac.uk).
    • 1. Absolute structure was checked using Friedel pairs and chemical information. CCDC-630533 (3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/conts/retrieving.html (or the Cambridge Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336.033; or deposit@ccdc.cam.ac.uk).
  • 52
    • 34848825487 scopus 로고    scopus 로고
    • 3), the pressure measured inside the flask was 1.15 bar.
    • 3), the pressure measured inside the flask was 1.15 bar.
  • 53
    • 1642322375 scopus 로고    scopus 로고
    • 2 by using chiral Salen Co(III)/quaternary ammonium halide as the catalyst system is described in: Lu, X. B.; Liang, B.; Tian, Y.-J.; Wang, Y. M.; Bai, C. X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732-3733.
    • 2 by using chiral Salen Co(III)/quaternary ammonium halide as the catalyst system is described in: Lu, X. B.; Liang, B.; Tian, Y.-J.; Wang, Y. M.; Bai, C. X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732-3733.
  • 54
    • 34848834654 scopus 로고    scopus 로고
    • 3.
    • 3.
  • 55
    • 34848856228 scopus 로고    scopus 로고
    • To explain the ring opening of amino epoxides 1 or 2 by other nucleophiles (refs 11-14), a direct attack of the nucleophiles to the oxirane ring, without participation of the dibenzylamino group, was proposed because the reaction took place (under the same reaction conditions) on epoxides without a dibenzylamino group.
    • To explain the ring opening of amino epoxides 1 or 2 by other nucleophiles (refs 11-14), a direct attack of the nucleophiles to the oxirane ring, without participation of the dibenzylamino group, was proposed because the reaction took place (under the same reaction conditions) on epoxides without a dibenzylamino group.
  • 56
    • 4544351364 scopus 로고    scopus 로고
    • The selective coordination of the Lewis acid with the epoxide instead of the nitrogen of dibenzylamino group is proposed on the basis of previous results. Thus, the treatment of dibenzylamino aziridines with BF3 and further treatment with lithium aluminium hydride afforded the corresponding complex aziridine-borane with total selectivity, and no complex of dibenzylamino-borane was detected on the crude reactions. The aziridine-borane complex was isolated, and its structure was established by single-crystal X-ray diffraction analysis: Concellón, J. M, Suárez, J. R, García-Granda, S, Díaz, M. R. Angew. Chem, Int. Ed. 2004, 43, 4333-4336
    • 3 and further treatment with lithium aluminium hydride afforded the corresponding complex aziridine-borane with total selectivity, and no complex of dibenzylamino-borane was detected on the crude reactions. The aziridine-borane complex was isolated, and its structure was established by single-crystal X-ray diffraction analysis: Concellón, J. M.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
  • 57
    • 13444309394 scopus 로고    scopus 로고
    • The same participation of the dibenzylamino group in ring-opening of amino epoxides by ketones was previously proposed: (a) Concellón, J. M, Suárez, J. R, García-Granda, S, Díaz, M. R. Org. Lett. 2005, 7, 247-250
    • The same participation of the dibenzylamino group in ring-opening of amino epoxides by ketones was previously proposed: (a) Concellón, J. M.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2005, 7, 247-250.
  • 58
    • 0043076447 scopus 로고    scopus 로고
    • A similar participation of the dibenzylamino group to justify the ring-opening of amino aziridines by various nucleophiles was also proposed: (b) Concellón, J. M, Riego, E. J. Org. Chem. 2003, 68, 6407-6410
    • A similar participation of the dibenzylamino group to justify the ring-opening of amino aziridines by various nucleophiles was also proposed: (b) Concellón, J. M.; Riego, E. J. Org. Chem. 2003, 68, 6407-6410.
  • 63
    • 34848830289 scopus 로고    scopus 로고
    • 2 with epoxides: refs 7a and 71 and references cited therein.
    • 2 with epoxides: refs 7a and 71 and references cited therein.


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