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Volumn , Issue 2, 2007, Pages 273-277

Copper-catalyzed enantioselective tandem conjugate addition/N-nitroso aldol reaction

Author keywords

hydroxyamino carbonyl compounds; Enantioselective; Monophosphoramidite; N nitroso aldol reaction; Tandem conjugate addition

Indexed keywords

ALPHA HYDROXYAMINO CARBONYL DERIVATIVE; CARBONYL DERIVATIVE; COPPER; KETONE; NITROSOBENZENE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847036695     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968012     Document Type: Article
Times cited : (24)

References (51)
  • 8
    • 33847034340 scopus 로고    scopus 로고
    • Alexakis, A. In Transition Metal Catalysed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; IUPAC Blackwell Science: Oxford, 1999, 303.
    • (a) Alexakis, A. In Transition Metal Catalysed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; IUPAC Blackwell Science: Oxford, 1999, 303.
  • 14
    • 0034803441 scopus 로고    scopus 로고
    • For Co-catalyzed 1,4-addition/aldol and Michael cyclization, see: (a) Baik, T.-G.; Luiz, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
    • For Co-catalyzed 1,4-addition/aldol and Michael cyclization, see: (a) Baik, T.-G.; Luiz, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
  • 16
    • 0037176242 scopus 로고    scopus 로고
    • For Rh-catalyzed 1,4-addition/aldol cyclization, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
    • For Rh-catalyzed 1,4-addition/aldol cyclization, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
  • 18
    • 0037139505 scopus 로고    scopus 로고
    • 3-catalyzed 1,4-addition/Michael cyclization, see: (a) Wang, L. C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
    • 3-catalyzed 1,4-addition/Michael cyclization, see: (a) Wang, L. C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
  • 21
    • 0037419835 scopus 로고    scopus 로고
    • For Rh-catalyzed 1,4-addition/aldol cyclization, see: Cauble, D. F.; Gipson, J. G.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
    • For Rh-catalyzed 1,4-addition/aldol cyclization, see: Cauble, D. F.; Gipson, J. G.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
  • 23
    • 33847079613 scopus 로고    scopus 로고
    • Angew. Chem. 1997, 109, 2773.
    • (1997) Chem , vol.109 , pp. 2773
    • Angew1
  • 37
    • 0037613521 scopus 로고    scopus 로고
    • For the enantioselective nitroso aldol reaction and related papers, see: a
    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 6038
    • Momiyama, N.1    Yamamoto, H.2
  • 50
    • 33847048566 scopus 로고    scopus 로고
    • Copper-Catalyzed Enantioselective Tandem Conjugate Addition/N-Nitroso-Aldol Reaction: Typical Procedure: Under an Ar atmosphere, a solution of Cu(OTf)2 (3.6 mg, 0.010 mmol) and the monodentate phosphoramidite (0.020 mmol) in toluene (1 mL) was stirred at r.t. for 1 h. The colorless solution was cooled, 20°C) and the ketone (0.50 mmol) and the diethylzinc solution (1.2 equiv) in hexane (1.0 M, 0.6 mL, 0.6 mmol) were added. After 3 h at -20°C, PhNO (80.2 mg, 0.75 mmol, 1.5 equiv) in anhyd toluene (1.5 mL) was added. After stirring the mixture for 18 h, sat. aq NH4Cl (10 mL) was added to the reaction mixture, and then the reaction mixture was extracted with EtOAc (3 x 10 mL, The combined organic phases were washed with brine and dried over Na2SO4. The solvent was then removed under vacuum. After purification by flash chromatography on silica gel PE-EtOAc, 200:1, the addition product 2a was obtained in 86
    • 2) = 13.95 min, 22.65 min].
  • 51
    • 33847072145 scopus 로고    scopus 로고
    • 2 = 0.804, final R indices [I > 2σ(I)] R1 = 0.0419, wR2 = 0.0853 (CCDC no. 618359).
    • 2 = 0.804, final R indices [I > 2σ(I)] R1 = 0.0419, wR2 = 0.0853 (CCDC no. 618359).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.