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Volumn 47, Issue 42, 2008, Pages 8108-8111

Asymmetric palladium-catalyzed intramolecular α-arylation of aldehydes

Author keywords

arylation; Aldehydes; Asymmetric catalysis; P ligands; Palladium

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; ENANTIOSELECTIVITY; LIGANDS; NETWORK PROTOCOLS; ORGANIC COMPOUNDS; PALLADIUM;

EID: 54049148627     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803809     Document Type: Article
Times cited : (95)

References (48)
  • 1
    • 0001521888 scopus 로고
    • a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
    • (1993) Chem. Rev , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 3
    • 0032473509 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 388-401;
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 388-401
  • 5
    • 0037541354 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1688-1690;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1688-1690
  • 14
    • 0035906503 scopus 로고    scopus 로고
    • For asymmetric α-arylation of amides: a
    • For asymmetric α-arylation of amides: a) S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402-3415;
    • (2001) J. Org. Chem , vol.66 , pp. 3402-3415
    • Lee, S.1    Hartwig, J.F.2
  • 19
    • 36148933735 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8484-8487.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 8484-8487
  • 20
    • 0037051609 scopus 로고    scopus 로고
    • For asymmetric α-arylation of lactones
    • For asymmetric α-arylation of lactones: D. J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500-3501.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 3500-3501
    • Spielvogel, D.J.1    Buchwald, S.L.2
  • 21
    • 33845579450 scopus 로고    scopus 로고
    • For asymmetric α-arylation of ketoesters
    • For asymmetric α-arylation of ketoesters: X. Xie, Y. Chen, D. Ma, J. Am. Chem. Soc. 2006, 128, 16050-16051.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16050-16051
    • Xie, X.1    Chen, Y.2    Ma, D.3
  • 22
    • 54049147544 scopus 로고    scopus 로고
    • Recently, asymmetric organocatalytic α-arylation of aldehydes using quinones as a coupling partner has been reported: a J. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2007, 119, 5616-5619;
    • Recently, asymmetric organocatalytic α-arylation of aldehydes using quinones as a coupling partner has been reported: a) J. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2007, 119, 5616-5619;
  • 23
    • 34547178180 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5520-5523.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 5520-5523
  • 27
    • 24944490141 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5705-5709;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 5705-5709
  • 29
    • 34948878232 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7236-7239;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 7236-7239
  • 31
    • 41949129532 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 2127-2130.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 2127-2130
  • 32
    • 54049101318 scopus 로고    scopus 로고
    • Other palladium sources tested: [Pd2(dba)3, Pd(dba)2, allyl)PdCl}2, and, Me-allyl)PdCl} 2, other bases tested: Na2CO3, K 2CO3, K3PO4, NaOtBu, KOtBu, and LiHMDS; other solvents tested: 1,4-dioxane, toluene, THF, DME, nBu2O, DMF, and MeCN
    • 2O, DMF, and MeCN.
  • 38
    • 0027180004 scopus 로고
    • The use of DABCO as decomplexating agent for borane complexes has been described
    • The use of DABCO as decomplexating agent for borane complexes has been described: H. Brisset, Y. Gourdel, P. Pellon, J. Le Corre, Tetrahedron Lett. 1993, 34, 4523-4526.
    • (1993) Tetrahedron Lett , vol.34 , pp. 4523-4526
    • Brisset, H.1    Gourdel, Y.2    Pellon, P.3    Le Corre, J.4
  • 39
    • 54049112451 scopus 로고    scopus 로고
    • When harsher reaction conditions were used (stronger inorganic bases such as NaOtBu or higher temperature) only decomposition of the starting material was obtained.
    • When harsher reaction conditions were used (stronger inorganic bases such as NaOtBu or higher temperature) only decomposition of the starting material was obtained.
  • 41
    • 54049091752 scopus 로고    scopus 로고
    • See Suporting Information for details
    • See Suporting Information for details.
  • 42
    • 54049096123 scopus 로고    scopus 로고
    • The absolute configuration of compounds 2i and 2j was assigned by analogy to the other compounds in Table 3 and Table 4.
    • The absolute configuration of compounds 2i and 2j was assigned by analogy to the other compounds in Table 3 and Table 4.
  • 43
    • 54049128695 scopus 로고    scopus 로고
    • This reaction is also known in the literature as the Pinnick oxidation: a B. O. Lindgren, T. Nilsson, Acta Chem. Scand. 1973, 27, 888-890;
    • This reaction is also known in the literature as the Pinnick oxidation: a) B. O. Lindgren, T. Nilsson, Acta Chem. Scand. 1973, 27, 888-890;
  • 45
    • 54049097305 scopus 로고    scopus 로고
    • For a discussion of the Lindgren/Pinnick oxidation nomenclature, see: J. Hayashida, V. H. Rawal, Angew. Chem. 2008, 120, 4445-4448;
    • For a discussion of the Lindgren/Pinnick oxidation nomenclature, see: J. Hayashida, V. H. Rawal, Angew. Chem. 2008, 120, 4445-4448;
  • 46
    • 46749145371 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4373-4376.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4373-4376


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.