메뉴 건너뛰기




Volumn 19, Issue 40, 2013, Pages 13547-13553

Cooperative catalysis of metal and O-H⋯O/sp3-C-H⋯O two-point hydrogen bonds in alcoholic solvents: Cu-catalyzed enantioselective direct alkynylation of aldehydes with terminal alkynes

Author keywords

asymmetric catalysis; cooperative catalysis; copper; density functional calculations; hydrogen bonds

Indexed keywords

ALCOHOLS; ALDEHYDES; CATALYSIS; CATALYSTS; COPPER; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HYDROCARBONS; LIGANDS; SOLVENTS; SUBSTRATES;

EID: 84884819280     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301280     Document Type: Article
Times cited : (41)

References (43)
  • 5
    • 38349189109 scopus 로고    scopus 로고
    • T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
    • (2007) Chem. Rev. , vol.107 , pp. 5744-5758
    • Akiyama, T.1
  • 10
    • 33845728625 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 8100-8102.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8100-8102
  • 12
    • 33845788846 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 8103-8104.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8103-8104
  • 13
    • 54549105366 scopus 로고    scopus 로고
    • The Noyori-Ikariya asymmetric transfer hydrogenation of ketones catalyzed by transition-metal amides and related catalysis are important exceptions; see ref. [3] and
    • The Noyori-Ikariya asymmetric transfer hydrogenation of ketones catalyzed by transition-metal amides and related catalysis are important exceptions; see ref. [3] and, C. Wang, X. Wu, J. Xiao, Chem. Asian J. 2008, 3, 1750-1770.
    • (2008) Chem. Asian J. , vol.3 , pp. 1750-1770
    • Wang, C.1    Wu, X.2    Xiao, J.3
  • 14
    • 66149109902 scopus 로고    scopus 로고
    • A review on the enantioselective alkynylation of carbonyl compounds and imines
    • A review on the enantioselective alkynylation of carbonyl compounds and imines:, B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963-983.
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 963-983
    • Trost, B.M.1    Weiss, A.H.2
  • 22
    • 77955830888 scopus 로고    scopus 로고
    • For a review on the enantioselective direct alkynylation of imines with terminal alkynes, see
    • For a review on the enantioselective direct alkynylation of imines with terminal alkynes, see:, P. de Armas, D. Tejedor, F. García-Tellado, Angew. Chem. 2010, 122, 1029-1032
    • (2010) Angew. Chem. , vol.122 , pp. 1029-1032
    • De Armas, P.1    Tejedor, D.2    García-Tellado, F.3
  • 23
    • 76249109420 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 1013-1016.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1013-1016
  • 36
    • 0035822774 scopus 로고    scopus 로고
    • For formyl C-H⋯O hydrogen bonds in enantioselective Lewis acid-catalyzed reactions of aldehydes, see
    • For formyl C-H⋯O hydrogen bonds in enantioselective Lewis acid-catalyzed reactions of aldehydes, see:, E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321-1329.
    • (2001) Chem. Commun. , pp. 1321-1329
    • Corey, E.J.1    Lee, T.W.2
  • 37
    • 77955827392 scopus 로고    scopus 로고
    • 3 C-H bond of N-acylimidazolinium salts and a carboxylate oxygen atom have been proposed for the enantioselective acyl transfer catalysis; see
    • 3 C-H bond of N-acylimidazolinium salts and a carboxylate oxygen atom have been proposed for the enantioselective acyl transfer catalysis; see:, I. Shiina, K. Nakata, K. Ono, Y. Onoda, M. Itagaki, J. Am. Chem. Soc. 2010, 132, 11629-11641.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11629-11641
    • Shiina, I.1    Nakata, K.2    Ono, K.3    Onoda, Y.4    Itagaki, M.5
  • 38
    • 23744479085 scopus 로고    scopus 로고
    • 2-C-H bond and a carboxylate oxygen atom have been proposed for acyl transfer catalysis with 4-(N,N-dimethylamino)pyridine (DMAP); see
    • 2-C-H bond and a carboxylate oxygen atom have been proposed for acyl transfer catalysis with 4-(N,N-dimethylamino)pyridine (DMAP); see:, S. Xu, I. Held, B. Kempf, H. Mayr, W. Steglich, H. Zipse, Chem. Eur. J. 2005, 11, 4751-4757.
    • (2005) Chem. Eur. J. , vol.11 , pp. 4751-4757
    • Xu, S.1    Held, I.2    Kempf, B.3    Mayr, H.4    Steglich, W.5    Zipse, H.6
  • 39
    • 84876499989 scopus 로고    scopus 로고
    • C-H⋯O interactions in cinchona alkaloid-catalyzed enantioselective methanolysis of meso-cyclic anhydrides:, 5818
    • C-H⋯O interactions in cinchona alkaloid-catalyzed enantioselective methanolysis of meso-cyclic anhydrides:, H. Yang, M. W. Wong, J. Am. Chem. Soc. 2013, 135, 5808-5818.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 5808
    • Yang, H.1    Wong, M.W.2
  • 41
    • 84884817125 scopus 로고    scopus 로고
    • N2-type O-alkylation reactions; the C-H bond is located at the pentagonal carbon center with a partial positive charge; see
    • N2-type O-alkylation reactions; the C-H bond is located at the pentagonal carbon center with a partial positive charge; see:, I. Čoric̈, J. H. Kim, T. Vlaar, M. Patil, W. Thiel, B. List, Angew. Chem. 2013, 125, 3574-3577
    • (2013) Angew. Chem. , vol.125 , pp. 3574-3577
    • Čoric̈, I.1    Kim, J.H.2    Vlaar, T.3    Patil, M.4    Thiel, W.5    List, B.6
  • 42
    • 84875136586 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2013, 52, 3490-3493.
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 3490-3493
  • 43
    • 84877055012 scopus 로고    scopus 로고
    • IV complexes coordinated with a tridentate pyridine ligand, see
    • IV complexes coordinated with a tridentate pyridine ligand, see:, A. Maleckis, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2013, 135, 6618-6625.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 6618-6625
    • Maleckis, A.1    Kampf, J.W.2    Sanford, M.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.