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Volumn 352, Issue 9, 2010, Pages 1434-1440

Simple preparation of dimeric cinchona alkaloid derivatives on polystyrene supports and a highly enantioselective catalytic heterogeneous dimerization of ketenes

Author keywords

Asymmetric catalysis; Cinchona alkaloids; Click chemistry; Ketene dimerization; Supported catalysts

Indexed keywords


EID: 77954303369     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000165     Document Type: Article
Times cited : (22)

References (58)
  • 3
    • 0003492617 scopus 로고    scopus 로고
    • General reviews on recoverable enantioselective catalysts: a (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim
    • General reviews on recoverable enantioselective catalysts: a) Chiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000;
    • (2000) Chiral Catalyst Immobilization and Recycling
  • 6
    • 33746840539 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4732-4762;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4732-4762
  • 9
    • 0141619399 scopus 로고    scopus 로고
    • Reviews on recoverable (asymmetric)organocatalysts: a
    • Reviews on recoverable (asymmetric)organocatalysts: a) M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401-3429;
    • (2003) Chem. Rev. , vol.103 , pp. 3401-3429
    • Benaglia, M.1    Puglisi, A.2    Cozzi, F.3
  • 12
    • 16444366385 scopus 로고    scopus 로고
    • and references cited therein. For subsequent developments, see
    • a) A. Mandoli, D. Pini, M. Fiori, P. Salvadori, Eur. J. Org. Chem. 2005, 1271-1282, and references cited therein. For subsequent developments, see:
    • (2005) Eur. J. Org. Chem. , pp. 1271-1282
    • Mandoli, A.1    Pini, D.2    Fiori, M.3    Salvadori, P.4
  • 31
    • 0002970514 scopus 로고    scopus 로고
    • For an approach relying on the functionalization of the central heterocyclic spacer, see: a
    • For an approach relying on the functionalization of the central heterocyclic spacer, see: a) C. Bolm, A. Gerlach, Chem. Commun. 1997, 2353-2354;
    • (1997) Chem. Commun. , pp. 2353-2354
    • Bolm, C.1    Gerlach, A.2
  • 34
  • 35
    • 34247237682 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1018-1025;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1018-1025
  • 46
    • 77954248839 scopus 로고    scopus 로고
    • Given the small difference in the nitrogen content between the azidomethyl resins P2a, b and the chiral derivatives 8 and 9, elemental analysis was generally not suitable for the estimation of alkaloid loading
    • Given the small difference in the nitrogen content between the azidomethyl resins P2a, b and the chiral derivatives 8 and 9, elemental analysis was generally not suitable for the estimation of alkaloid loading.
  • 47
    • 77954264283 scopus 로고    scopus 로고
    • IPB pyridazine derivatives had been used before for asymmetric osmium-mediated oxidations. Nonetheless, the underlying polystyrene matrix of P3a, b and P4a, b makes these materials poorly compatible with the required protic reaction media. This was confirmed in preliminary styrene AD runs with P4a and P4b, where relatively low ee values (17-85%) were obtained
    • IPB pyridazine derivatives had been used before for asymmetric osmium-mediated oxidations. Nonetheless, the underlying polystyrene matrix of P3a, b and P4a, b makes these materials poorly compatible with the required protic reaction media. This was confirmed in preliminary styrene AD runs with P4a and P4b, where relatively low ee values (17-85%) were obtained.
  • 56
    • 77954283663 scopus 로고    scopus 로고
    • Standard filtration experiments excluded the presence of any significant catalytic activity in the solution (Supporting Information)
    • Standard filtration experiments excluded the presence of any significant catalytic activity in the solution (Supporting Information).
  • 57
    • 77954304807 scopus 로고    scopus 로고
    • It should be noted, however, that under Calter's conditions the rate-limiting event is the deprotonation of 12 by DIPEA, to give the corresponding ketene; variations of the alkaloid catalytic activity in the dimerization step could be, therefore, largely shadowed by this fact
    • It should be noted, however, that under Calter's conditions the rate-limiting event is the deprotonation of 12 by DIPEA, to give the corresponding ketene; variations of the alkaloid catalytic activity in the dimerization step could be, therefore, largely shadowed by this fact.
  • 58
    • 77954287968 scopus 로고    scopus 로고
    • For the sake of comparison, the use of QD-TMS under the literature conditions (5mol%) provides P= 7.9 @ 97% ee (see Table 2); the reduction of the catalyst loading to 1 mol% allows some increase in the productivity, albeit at the expenses of product yield (50% ) and enantiomeric purity (P=25 @ 93% ee, this work)
    • For the sake of comparison, the use of QD-TMS under the literature conditions (5mol%) provides P= 7.9 @ 97% ee (see Table 2); the reduction of the catalyst loading to 1 mol% allows some increase in the productivity, albeit at the expenses of product yield (50% ) and enantiomeric purity (P=25 @ 93% ee, this work).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.