메뉴 건너뛰기




Volumn 356, Issue 8, 2014, Pages 1708-1718

Modular synthesis of Ar-BINMOL-phos for catalytic asymmetric alkynylation of aromatic aldehydes with unexpected reversal of enantioselectivity

Author keywords

alkynylation; asymmetric catalysis; chiral ligands; chirality inversion; phosphines

Indexed keywords


EID: 84901267525     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201301128     Document Type: Article
Times cited : (43)

References (108)
  • 3
    • 77949627101 scopus 로고    scopus 로고
    • references cited therein.
    • M. Bartõk, Chem. Rev. 2010, 110, 1663-1705, and references cited therein.
    • (2010) Chem. Rev. , vol.110 , pp. 1663-1705
    • Bartõk, M.1
  • 5
    • 77950466555 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2772-2776.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2772-2776
  • 7
    • 78650084572 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 9384-9387.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9384-9387
  • 12
    • 84861602561 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 5706-5710.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 5706-5710
  • 14
    • 84856154201 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 1187-1190
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1187-1190
  • 23
    • 79961233987 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 7681-7685
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7681-7685
  • 44
    • 0242635970 scopus 로고    scopus 로고
    • L. Pu, Tetrahedron 2003, 59, 9873-9886
    • (2003) Tetrahedron , vol.59 , pp. 9873-9886
    • Pu, L.1
  • 66
    • 84863223734 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 6704-6708
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6704-6708
  • 79
  • 81
    • 84901274849 scopus 로고    scopus 로고
    • Sawamura and co-workers have reported firstly an example of enantioselective alkynylation of aldehydes with promising enantioselectivity (up to 56% ee) in the presence of a copper-phosphine complex
    • Sawamura and co-workers have reported firstly an example of enantioselective alkynylation of aldehydes with promising enantioselectivity (up to 56% ee) in the presence of a copper-phosphine complex
  • 82
    • 35048854040 scopus 로고    scopus 로고
    • 3-C-HO hydrogen bond plays an important role in a highly directional catalyst-substrate interaction
    • 3-C-HO hydrogen bond plays an important role in a highly directional catalyst-substrate interaction
    • (2007) Org. Lett. , vol.9 , pp. 3901-3904
    • Asano, Y.1    Hara, K.2    Ito, H.3    Sawamura, M.4
  • 85
    • 84901261894 scopus 로고    scopus 로고
    • The preparation and characterization of Ar-BINMOL-derived monophosphine ligand L3 is provided in the Supporting Information.
    • The preparation and characterization of Ar-BINMOL-derived monophosphine ligand L3 is provided in the Supporting Information.
  • 87
    • 77953521328 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2410-2413
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2410-2413
  • 90
  • 91
    • 84883213575 scopus 로고    scopus 로고
    • 3 central chirality from BINOL and chiral amine was found to be an efficient ligand in the enantioselective copper-catalyzed conjugate addition of organic zinc reagent to enones with excellent enantioselectivities and TON (high TON of 17600 and up to 99% ee), see.
    • 3 central chirality from BINOL and chiral amine was found to be an efficient ligand in the enantioselective copper-catalyzed conjugate addition of organic zinc reagent to enones with excellent enantioselectivities and TON (high TON of 17600 and up to 99% ee), see:, F. Ye, Z. J. Zheng, W. H. Deng, L. S. Zheng, Y. Deng, C. G. Xia, L. W. Xu, Chem. Asian J. 2013, 8, 2242-2253.
    • (2013) Chem. Asian J. , vol.8 , pp. 2242-2253
    • Ye, F.1    Zheng, Z.J.2    Deng, W.H.3    Zheng, L.S.4    Deng, Y.5    Xia, C.G.6    Xu, L.W.7
  • 95
    • 0032538773 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2922-2959
  • 102
    • 84858024215 scopus 로고    scopus 로고
    • similarly, about magnesium binaphtholates, see
    • Y. Yamashita, T. Tsubogo, S. Kobayashi, Chem. Sci. 2012, 3, 967-975; similarly, about magnesium binaphtholates, see
    • (2012) Chem. Sci. , vol.3 , pp. 967-975
    • Yamashita, Y.1    Tsubogo, T.2    Kobayashi, S.3
  • 104
    • 84876472096 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2013, 52, 4549-4554.
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4549-4554
  • 105
    • 84876270859 scopus 로고    scopus 로고
    • Recently, Krenske and Houk have summarized and reported the important role of attractive non-covalent interaction of aromatic rings in many catalytic enantioselective transformations.
    • Recently, Krenske and Houk have summarized and reported the important role of attractive non-covalent interaction of aromatic rings in many catalytic enantioselective transformations:, E. H. Krenske, K. N. Houk, Acc. Chem. Res. 2013, 46, 979-989.
    • (2013) Acc. Chem. Res. , vol.46 , pp. 979-989
    • Krenske, E.H.1    Houk, K.N.2
  • 106


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.