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Volumn 129, Issue 21, 2007, Pages 6686-6687

Catalytic enantioselective petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE; THIOUREA DERIVATIVE;

EID: 34249793225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071470x     Document Type: Article
Times cited : (256)

References (41)
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    • 4344713238 scopus 로고    scopus 로고
    • For discussions on activation of N-acyl iminium ion by thiourea, see: (a) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
    • For discussions on activation of N-acyl iminium ion by thiourea, see: (a) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
  • 27
    • 4544221552 scopus 로고    scopus 로고
    • For recent reviews on organocatalyst, see: a
    • For recent reviews on organocatalyst, see: (a) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 2062
    • Pihko, P.M.1
  • 29
    • 4143094833 scopus 로고    scopus 로고
    • Houk, K. N, List, B, Eds, special issue on organocatalysis
    • (c) Houk, K. N., List, B., Eds. Acc. Chem. Res. 2004, 37, 487 special issue on organocatalysis.
    • (2004) Acc. Chem. Res , vol.37 , pp. 487
  • 34
    • 34247164504 scopus 로고    scopus 로고
    • Urea catalyst with a sulfinamide moiety was recently reported to promote allylation of acylhydrazones using an indium reagent. See: Tan, K. L, Jacobsen, E. N. Angew. Chem, Int. Ed. 2007, 46, 1315
    • Urea catalyst with a sulfinamide moiety was recently reported to promote allylation of acylhydrazones using an indium reagent. See: Tan, K. L.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 1315.
  • 35
    • 34249814079 scopus 로고    scopus 로고
    • 2 and toluene.
    • 2 and toluene.
  • 36
    • 34249828717 scopus 로고    scopus 로고
    • 2O instead of chloroformate led to lower ee.
    • 2O instead of chloroformate led to lower ee.
  • 38
    • 34249814961 scopus 로고    scopus 로고
    • The results of reactions using catalysts 1d-g are given in the Supporting Information.
    • The results of reactions using catalysts 1d-g are given in the Supporting Information.
  • 39
    • 34249800148 scopus 로고    scopus 로고
    • 2OH as a proton source was less effective and led to a lower ee.
    • 2OH as a proton source was less effective and led to a lower ee.
  • 40
    • 34249809180 scopus 로고    scopus 로고
    • A similar trend was observed in the reaction of another quinoline 2b. Thus, the use of H2O and NaHCO3 was found to be optimal for not only enantioselectivity but also chemical efficiency
    • 3 was found to be optimal for not only enantioselectivity but also chemical efficiency.
  • 41
    • 34249795531 scopus 로고    scopus 로고
    • The reaction with arylboronic acids bearing phenyl and p-methoxyphenyl groups gave no desired products owing to their low reactivities.
    • The reaction with arylboronic acids bearing phenyl and p-methoxyphenyl groups gave no desired products owing to their low reactivities.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.