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Tetrahedron Asymmetry
Volumn 11, Issue 20, 2000, Pages 4039-4042
Heterogeneous asymmetric catalytic aminohydroxylation promoted by a bis-Cinchona alkaloid derivative supported onto an insoluble organic polymeric matrix
Author keywords

[No Author keywords available]
Indexed keywords

CINNAMIC ACID DERIVATIVE; PHTHALAZINE DERIVATIVE; QUININE DERIVATIVE;
EID: 0034692897     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00399-2     Document Type: Article
Times cited : (29)
References (6)
  • 1
    • 0007256094 scopus 로고    scopus 로고
    • (a) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (b) See also: O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326 and references cited therein.
  • 2
    • 0007189186 scopus 로고    scopus 로고
    • An example of highly enantioselective (88-99% e.e.) heterogeneous AA, by the use of silica gel supported quinine phthalazine ether, has been reported: Song, C. E.; Rim Oh, C.; Woo Lee, S.; Lee, S.; Canali, L.; Sherrington, D. C. Chem. Commun. 1998, 2435.
  • 4
    • 0007175184 scopus 로고    scopus 로고
    • (a) Salvadori, P.; Pini, D.; Petri, A. Synlett 1999, 1181. (b) Ronchi, F. Thesis, Universita di Pisa, Italy, 1998.
  • 5
    • 0007320009 scopus 로고    scopus 로고
    • Prepared by a published procedure, with modifications: Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Lett. 1994, 35, 6559.
  • 6
    • 0007246596 scopus 로고    scopus 로고
    • One could argue that the catalysis with P1 takes place in the homogeneous phase because of the ligand leaching under the reaction conditions. In this respect it is interesting to note that the solutions obtained by filtering the aged suspensions of the polymeric alkaloid alone in the pure solvent, or in the presence of Chloramine-M, contained only minute amounts of the ligand (less than 0.5% of the total supported alkaloid, by UV analysis). Accordingly, after the addition of the lacking reagents to these filtrates, the AA reaction proceeded with regio- and enantioselectivity values (66-69% and 23-34%, respectively) much lower than those obtained in the presence of P1. Furthermore, after P1 had been filtered off at 55% conversion in an AA test run, a substantial worsening of the selectivity was observed (76% regioselectivity and 34% enantioselectivity after the filtration).

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