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Volumn 47, Issue 40, 2008, Pages 7656-7658

Primary-amine-catalyzed enantioselective intramolecular aldolizations

Author keywords

Aldol reaction; Asymmetric catalysis; Bifunctional catalysis; Enamines; Organocatalysis

Indexed keywords


EID: 54649084880     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802497     Document Type: Article
Times cited : (145)

References (49)
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    • Z. G. Hajos, D. R. Parrish, Germany Patent DE 21022623, 1971;
    • a) Z. G. Hajos, D. R. Parrish, Germany Patent DE 21022623, 1971;
  • 4
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    • U. Eder, G. R. Sauer, R. Wiechert, Germany Patent DE 2014757, 1971;
    • b) U. Eder, G. R. Sauer, R. Wiechert, Germany Patent DE 2014757, 1971;
  • 14
    • 0017156419 scopus 로고    scopus 로고
    • For examples of asymmetric enamine catalysis using primary amines, see: a S. Danishefsky, P. Cain, J. Am. Chem. Soc. 1976, 98, 4975-4983;
    • For examples of asymmetric enamine catalysis using primary amines, see: a) S. Danishefsky, P. Cain, J. Am. Chem. Soc. 1976, 98, 4975-4983;
  • 25
    • 44949251617 scopus 로고    scopus 로고
    • For a review on primary amino acids as catalysts, see: l
    • For a review on primary amino acids as catalysts, see: l) L.-W. Xu, Y. Lu, Org. Biomol. Chem. 2008, 6, 2047-2053.
    • (2008) Org. Biomol. Chem , vol.6 , pp. 2047-2053
    • Xu, L.-W.1    Lu, Y.2
  • 26
    • 23044486704 scopus 로고    scopus 로고
    • For examples of asymmetric iminium ion catalysis using primary amines, see: a K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505;
    • For examples of asymmetric iminium ion catalysis using primary amines, see: a) K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505;
  • 30
    • 33846463775 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 389-392;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 389-392
  • 34
    • 27644456225 scopus 로고    scopus 로고
    • For enamine catalysis of intermolecular aldolizations of ketones, see: a
    • For enamine catalysis of intermolecular aldolizations of ketones, see: a) O. Tokuda, T. Kano, W.-G. Gao, T. Ikemoto, K. Maruoka, Org. Lett. 2005, 7, 5103-5105;
    • (2005) Org. Lett , vol.7 , pp. 5103-5105
    • Tokuda, O.1    Kano, T.2    Gao, W.-G.3    Ikemoto, T.4    Maruoka, K.5
  • 40
    • 34548367558 scopus 로고    scopus 로고
    • CH3CO2H (pKa =4.76, e.r, 28.1, PhCO2H (pKa, 4.31, e.r, 17.8, Cl 3CCO2H (pKa, 0.65, e.r, 16.5, CF3CO2H (pKa, 0.25, e.r, 9.8, pTsOH pKa, 2.80, e.r, 4.9, For a discussion of acid co-catalyst effects in enamine catalytic aldolizations, see: A. Erkkilä, P. M. Pihko, Eur. J. Org. Chem. 2007, 4205-4216
    • a = -2.80, e.r. = 4.9). For a discussion of acid co-catalyst effects in enamine catalytic aldolizations, see: A. Erkkilä, P. M. Pihko, Eur. J. Org. Chem. 2007, 4205-4216.
  • 45
    • 54749099277 scopus 로고    scopus 로고
    • For the one-step synthesis of diketone 2a, see the Supporting Information.
    • For the one-step synthesis of diketone 2a, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.