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Volumn 44, Issue 25, 2005, Pages 3881-3884

Enantioselective Henry reactions under dual Lewis acid/amine catalysis using chiral amino alcohol ligands

Author keywords

Amines; Amino alcohols; Asymmetric catalysis; Henry reaction; Lewis acids

Indexed keywords

ALDEHYDES; CATALYSIS; CHEMICAL ACTIVATION; STOICHIOMETRY; SUBSTITUTION REACTIONS;

EID: 21244472399     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200463075     Document Type: Article
Times cited : (231)

References (48)
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    • For enantioselective fluoride-mediated Henry reactions that used silyl nitronates as preactivated forms of nitroalkanes, see: a) T. Risgaard, K. V. Gothelf, K. A. Jørgensen, Org. Biomol. Chem. 2003, 1, 153-156;
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    • see Ref. [10b]
    • Base-catalyzed, nonselective Henry reactions are long known. For the incidence of such a process in the efficiency of asymmetric catalysis, see Ref. [10b].
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    • Ligand 10 was prepared by the reductive methylation of indanol. See: S. Yao, J.-C. Meng, G. Siuzdak, M. G. Finn, J. Org. Chem. 2003, 68, 2540-2546. The remaining ligands were purchased from Aldrich.
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    • note
    • Other combinations of metal salts and Brønsted bases were also examined, with either inferior results or complete failure of the reaction observed. See Supporting Information for more details.
  • 42
    • 21244449819 scopus 로고    scopus 로고
    • note
    • 2EtN/(+)-NME (10:10:15 mol % each) led to product 3d in 75 % yield and in 90 % ee.
  • 43
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    • note
    • Under the optimized conditions for nitromethane, the reaction between nitroethane and benzaldehyde gave a mixture of antiand syn-nitroaldols in a 65:35 ratio.
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    • note
    • Similar results have also been observed in reactions with butyraldehyde and heptanal. See Supporting Information for details.
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    • note
    • [7]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.