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Volumn 133, Issue 12, 2011, Pages 4260-4263

Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; BENZYLIC; CATALYTIC CONDITIONS; DIARYLIODONIUM SALTS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CONSTRUCTION; IODONIUM SALTS; KETOPROFEN; NEW STRATEGY; ORGANIC CATALYSTS; ORGANOCATALYSIS; RAPID SYNTHESIS; STEREOCENTERS; SYNTHONS;

EID: 79953035867     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2008906     Document Type: Article
Times cited : (266)

References (46)
  • 1
    • 0033582999 scopus 로고    scopus 로고
    • For racemic α-arylation of carbonyl compounds, see
    • For racemic α-arylation of carbonyl compounds, see: Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2355
    • Muratake, H.1    Nakai, H.2
  • 4
  • 13
  • 32
    • 33751499126 scopus 로고
    • Reactions with silyl enol ethers require the diaryliodonium fluoride in the absence of other additives; see
    • Reactions with silyl enol ethers require the diaryliodonium fluoride in the absence of other additives; see: Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764
    • (1991) J. Org. Chem. , vol.56 , pp. 5764
    • Chen, K.1    Koser, G.F.2
  • 34
    • 46049110936 scopus 로고    scopus 로고
    • For examples of copper-catalyzed arylation reactions, see
    • For examples of copper-catalyzed arylation reactions, see: Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8172
    • Phipps, R.J.1    Grimster, N.P.2    Gaunt, M.J.3
  • 38
    • 0000872895 scopus 로고
    • For studies on the mechanism of copper-catalyzed arylation, see
    • For studies on the mechanism of copper-catalyzed arylation, see: Lockhart, T. P. J. Am. Chem. Soc. 1983, 105, 1940
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1940
    • Lockhart, T.P.1
  • 40
    • 79953053781 scopus 로고    scopus 로고
    • 3 is necessary to remove the trifluoromethanesulfonic acid that is formed during the reaction.
    • 3 is necessary to remove the trifluoromethanesulfonic acid that is formed during the reaction.
  • 41
    • 79953033314 scopus 로고    scopus 로고
    • The isolated α-formyl adducts are generally stable at room temperature without significant racemization. 2-Phenyloctanal was isolated with 90% ee through direct purification by flash chromatography (see Supporting Information). Rechecking the enantiopurity of the 2-phenyloctanal after 3 weeks confirmed the initial 90% ee (i.e., no erosion in optical purity).
    • The isolated α-formyl adducts are generally stable at room temperature without significant racemization. 2-Phenyloctanal was isolated with 90% ee through direct purification by flash chromatography (see Supporting Information). Rechecking the enantiopurity of the 2-phenyloctanal after 3 weeks confirmed the initial 90% ee (i.e., no erosion in optical purity).
  • 42
    • 19744365933 scopus 로고    scopus 로고
    • Sanford and co-workers also used this approach in the Pd-catalyzed arylation of C-H bonds, see
    • Sanford and co-workers also used this approach in the Pd-catalyzed arylation of C-H bonds, see: Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 7330
    • Kalyani, D.1    Deprez, N.R.2    Desai, L.V.3    Sanford, M.S.4
  • 44
    • 77952637874 scopus 로고    scopus 로고
    • For a review on the merger of organocatalysis and transition metal catalysis for tandem catalytic activation, see
    • For a review on the merger of organocatalysis and transition metal catalysis for tandem catalytic activation, see: Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999
    • (2010) Eur. J. Org. Chem. , pp. 2999
    • Zhong, C.1    Shi, X.2
  • 45
    • 79953066881 scopus 로고    scopus 로고
    • DFT calculations for the enamine were performed with the use of B3LYP/6-311+G(2d,2p)//B3LYP/6-31G(d). The arylcopper(III) species was not included in the DFT calculation.
    • DFT calculations for the enamine were performed with the use of B3LYP/6-311+G(2d,2p)//B3LYP/6-31G(d). The arylcopper(III) species was not included in the DFT calculation.
  • 46
    • 79953046657 scopus 로고    scopus 로고
    • Department of Chemistry, University of Arizona. Top 200 Pharmaceutical Products by Worldwide Sales in 2009. (accessed Jan).
    • Mack, D. J.; Brichacek, M.; Plichta, A.; Njardarson, J. T. Department of Chemistry, University of Arizona. Top 200 Pharmaceutical Products by Worldwide Sales in 2009. http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals- poster (accessed Jan 2011).
    • (2011)
    • MacK, D.J.1    Brichacek, M.2    Plichta, A.3    Njardarson, J.T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.