메뉴 건너뛰기




Volumn 44, Issue 4, 2012, Pages 489-503

Transition-metal-catalyzed enantioselective propargylic substitution reactions of propargylic alcohol derivatives with nucleophiles

Author keywords

alkylation; enantioselective reaction; nucleophile; organocatalyst; propargylic alcohol; propargylic substitution reaction

Indexed keywords

2-NAPHTHOLS; ASYMMETRIC REACTION; COPPER CATALYST; CYCLOADDITIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE REACTIONS; ETHYNYL; LEWIS ACID CATALYSTS; MISCELLANEOUS REACTIONS; ORGANOCATALYSTS; PROPARGYLATION; PROPARGYLIC ALCOHOLS; PROPARGYLIC SUBSTITUTION REACTIONS; RING OPENING REACTION; RUTHENIUM CATALYSTS; TRANSITION METAL CATALYSTS;

EID: 84857033087     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290158     Document Type: Review
Times cited : (199)

References (118)
  • 8
    • 0003799267 scopus 로고
    • Stang P. J. Diederich F. VCH Weinheim
    • Modern Acetylene Chemistry Stang P J. Diederich F VCH Weinheim 1995
    • (1995) Modern Acetylene Chemistry
  • 9
    • 21244469739 scopus 로고    scopus 로고
    • Diederich F. Stang P. J. Tykwinski R. R. Wiley-VCH Weinheim
    • Acetylene Chemistry Diederich F Stang P J. Tykwinski R R. Wiley-VCH Weinheim 2005
    • (2005) Acetylene Chemistry
  • 13
    • 33845281351 scopus 로고
    • For recent reviews, see
    • For recent reviews, see:, Nicholas K M., Acc. Chem. Res. 1987 20 207
    • (1987) Acc. Chem. Res. , vol.20 , pp. 207
    • Nicholas, K.M.1
  • 18
    • 0001549944 scopus 로고
    • Asymmetric versions of the Nicholas reaction have already been reported, see
    • Asymmetric versions of the Nicholas reaction have already been reported, see:, Nicholas K M., Mulvaney M, Bayer M, J. Am. Chem. Soc. 1980 102 2508
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2508
    • Nicholas, K.M.1    Mulvaney, M.2    Bayer, M.3
  • 20
    • 23844447350 scopus 로고    scopus 로고
    • As an alternative to the enantioselective Nicholas reaction, a stepwise propargylic alkylation of propargylic alcohols has been reported by using a stoichiometric amount of ruthenium complexes bearing an optically active diphosphine such as BINAP. See
    • As an alternative to the enantioselective Nicholas reaction, a stepwise propargylic alkylation of propargylic alcohols has been reported by using a stoichiometric amount of ruthenium complexes bearing an optically active diphosphine such as BINAP. See:, Nishibayashi Y, Imajima H, Onodera G, Uemura S, Organometallics 2005 24 4106
    • (2005) Organometallics , vol.24 , pp. 4106
    • Nishibayashi, Y.1    Imajima, H.2    Onodera, G.3    Uemura, S.4
  • 34
    • 33745777313 scopus 로고    scopus 로고
    • For recent reviews of transition-metal-allenylidene complexes, see
    • For recent reviews of transition-metal-allenylidene complexes, see:, Bruneau C, Dixneuf P H., Angew. Chem. Int. Ed. 2006 45 2176
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2176
    • Bruneau, C.1    Dixneuf, P.H.2
  • 41
    • 33646074054 scopus 로고    scopus 로고
    • For reviews on catalytic propargylic substitution reactions, see
    • For reviews on catalytic propargylic substitution reactions, see:, Nishibayashi Y, Uemura S, Curr. Org. Chem. 2006 10 135
    • (2006) Curr. Org. Chem. , vol.10 , pp. 135
    • Nishibayashi, Y.1    Uemura, S.2
  • 51
    • 21944455278 scopus 로고    scopus 로고
    • references cited therein
    • Hidai M, Mizobe Y, Can. J. Chem. 2005 83 358; and references cited therein
    • (2005) Can. J. Chem. , vol.83 , pp. 358
    • Hidai, M.1    Mizobe, Y.2
  • 57
    • 21744461509 scopus 로고    scopus 로고
    • The result of the density functional theory calculation on the model reaction also supports the proposed reaction pathway of the ruthenium-catalyzed propargylic substitution reactions of propargylic alcohols with nucleophiles, where ruthenium-allenylidene complexes work as key intermediates. See
    • The result of the density functional theory calculation on the model reaction also supports the proposed reaction pathway of the ruthenium-catalyzed propargylic substitution reactions of propargylic alcohols with nucleophiles, where ruthenium-allenylidene complexes work as key intermediates. See:, Ammal S C., Yoshikai N, Inada Y, Nishibayashi Y, Nakamura E, J. Am. Chem. Soc. 2005 127 9428
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 9428
    • Ammal, S.C.1    Yoshikai, N.2    Inada, Y.3    Nishibayashi, Y.4    Nakamura, E.5
  • 69
    • 84891005153 scopus 로고    scopus 로고
    • For a recent review, see: Bandini M. Umani-Ronchi A. Wiley-VCH Weinheim
    • For a recent review, see: Catalytic Asymmetric Friedel-Crafts Alkylations Bandini M Umani-Ronchi A Wiley-VCH Weinheim 2009
    • (2009) Catalytic Asymmetric Friedel-Crafts Alkylations
  • 81
    • 84857035501 scopus 로고    scopus 로고
    • Prof. vanMaarseveen and co-workers achieved the first enantioselective propargylic amination and presented a part of their result at the PAC Symposium 2007 (March 1, 2007, Utrecht).
    • Prof. vanMaarseveen and co-workers achieved the first enantioselective propargylic amination and presented a part of their result at the PAC Symposium 2007 (March 1, 2007, Utrecht).
  • 84
    • 70349967592 scopus 로고    scopus 로고
    • No copper-allenylidene complex has been isolated to date, but the first example of a silver-allenylidene complex was reported in 2009
    • No copper-allenylidene complex has been isolated to date, but the first example of a silver-allenylidene complex was reported in 2009:, Asay M, Donnadieu B, Schoeller W W., Bertrand G, Angew. Chem. Int. Ed. 2009 48 4796
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 4796
    • Asay, M.1    Donnadieu, B.2    Schoeller, W.W.3    Bertrand, G.4
  • 85
    • 61849156759 scopus 로고    scopus 로고
    • The first example of a palladium-allenylidene complex was also reported in 2009
    • The first example of a palladium-allenylidene complex was also reported in 2009:, Kessler F, Szesni N, Põhako K, Weibert B, Fischer H, Organometallics 2009 28 348
    • (2009) Organometallics , vol.28 , pp. 348
    • Kessler, F.1    Szesni, N.2    Põhako, K.3    Weibert, B.4    Fischer, H.5
  • 92
    • 47749122232 scopus 로고    scopus 로고
    • For recent reviews, see: Berkessel A. Gröger H. Wiley-VCH Weinheim
    • For recent reviews, see: Asymmetric Organocatalysis Berkessel A Gröger H Wiley-VCH Weinheim 2005
    • (2005) Asymmetric Organocatalysis
  • 94
    • 77950261392 scopus 로고    scopus 로고
    • List B. Springer Heidelberg
    • Asymmetric Organocatalysis List B Springer Heidelberg 2010
    • (2010) Asymmetric Organocatalysis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.