메뉴 건너뛰기




Volumn 38, Issue 20, 1999, Pages 3047-3050

Novel catalytic hydrogenolysis of trimethylsilyl enol ethers by the use of an acidic ruthenium dihydrogen complex

Author keywords

Asymmetric synthesis; Enols; Protonations; Ruthenium; Silicon

Indexed keywords

RUTHENIUM DIHYDROGEN; TRIMETHYLSILYL ENOL ETHER; TUNGSTEN; UNCLASSIFIED DRUG;

EID: 0033581551     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3047::AID-ANIE3047>3.0.CO;2-F     Document Type: Article
Times cited : (26)

References (35)
  • 3
    • 0033531383 scopus 로고    scopus 로고
    • For recent examples, see: a) A. C. Ontko, J. F. Houlis, R. C. Schnabel, D. M. Roddick, T. P. Fong, A. J. Lough, R. H. Morris, Organometallics 1998, 17, 5467; b) D. H. Lee, B. P. Patel, E. Clot, O. Eisenstein, R. H. Crabtree, Chem. Commun. 1999, 297; c) Z. Xu, I. Bytheway, G. Jia, Z. Lin, Organometallics 1999, 18, 1761.
    • (1999) Chem. Commun. , pp. 297
    • Lee, D.H.1    Patel, B.P.2    Clot, E.3    Eisenstein, O.4    Crabtree, R.H.5
  • 4
    • 0001582152 scopus 로고    scopus 로고
    • For recent examples, see: a) A. C. Ontko, J. F. Houlis, R. C. Schnabel, D. M. Roddick, T. P. Fong, A. J. Lough, R. H. Morris, Organometallics 1998, 17, 5467; b) D. H. Lee, B. P. Patel, E. Clot, O. Eisenstein, R. H. Crabtree, Chem. Commun. 1999, 297; c) Z. Xu, I. Bytheway, G. Jia, Z. Lin, Organometallics 1999, 18, 1761.
    • (1999) Organometallics , vol.18 , pp. 1761
    • Xu, Z.1    Bytheway, I.2    Jia, G.3    Lin, Z.4
  • 5
    • 2142774500 scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1992) Coord. Chem. Rev. , vol.121 , pp. 155
    • Jessop, P.G.1    Morris, R.H.2
  • 6
    • 0000420682 scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1993) Chem. Rev. , vol.93 , pp. 913
    • Heinekey, D.M.1    Oldham, W.J.2
  • 7
    • 0030288648 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1996) Can. J. Chem. , vol.74 , pp. 1907
    • Morris, R.H.1
  • 8
    • 0000562373 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1998) J Organomet. Chem. , vol.577 , pp. 111
    • Crabtree, R.H.1
  • 9
    • 0000776208 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1998) Chem. Rev. , vol.98 , pp. 2077
    • Sabo-Etienne, S.1    Chaudret, B.2
  • 10
    • 0032023408 scopus 로고    scopus 로고
    • For recent reviews, see: a) P. G. Jessop, R. H. Morris, Coord. Chem. Rev. 1992, 121, 155; b) D.M. Heinekey, W. J. Oldham, Chem. Rev. 1993, 93, 913; c) R. H. Morris, Can. J. Chem. 1996, 74, 1907; d) R. H. Crabtree, J Organomet. Chem. 1998, 577, 111; e) S. Sabo-Etienne, B. Chaudret, Chem. Rev. 1998, 98, 2077; f) M. A. Esteruelas, L. A. Oro, Chem. Rev. 1998, 98, 577.
    • (1998) Chem. Rev. , vol.98 , pp. 577
    • Esteruelas, M.A.1    Oro, L.A.2
  • 16
    • 0001087692 scopus 로고
    • 2) complexes in catalytic hydrogenation are found in the following articles: a) C. Bianchini, A. Meli, M. Peruzzini, P. Frediani, C. Bohanna, M. A. Esteruelas, L. A. Oro, Organometallics 1992, 11, 138; b) C. Bianchini, C. Bohanna, M. A. Esteruelas, P Frediani, A. Meli, L. A. Oro, M. Peruzzini, Organometallics 1992, 11, 3837; c) M. A. Esteruelas, J. Herrero, A. M. Lopez, L. A. Oro, M. Schulz, H. Werner, Inorg. Chem. 1992, 31, 4013.
    • (1992) Organometallics , vol.11 , pp. 138
    • Bianchini, C.1    Meli, A.2    Peruzzini, M.3    Frediani, P.4    Bohanna, C.5    Esteruelas, M.A.6    Oro, L.A.7
  • 17
    • 0000093525 scopus 로고
    • 2) complexes in catalytic hydrogenation are found in the following articles: a) C. Bianchini, A. Meli, M. Peruzzini, P. Frediani, C. Bohanna, M. A. Esteruelas, L. A. Oro, Organometallics 1992, 11, 138; b) C. Bianchini, C. Bohanna, M. A. Esteruelas, P Frediani, A. Meli, L. A. Oro, M. Peruzzini, Organometallics 1992, 11, 3837; c) M. A. Esteruelas, J. Herrero, A. M. Lopez, L. A. Oro, M. Schulz, H. Werner, Inorg. Chem. 1992, 31, 4013.
    • (1992) Organometallics , vol.11 , pp. 3837
    • Bianchini, C.1    Bohanna, C.2    Esteruelas, M.A.3    Frediani, P.4    Meli, A.5    Oro, L.A.6    Peruzzini, M.7
  • 18
    • 33751391590 scopus 로고
    • 2) complexes in catalytic hydrogenation are found in the following articles: a) C. Bianchini, A. Meli, M. Peruzzini, P. Frediani, C. Bohanna, M. A. Esteruelas, L. A. Oro, Organometallics 1992, 11, 138; b) C. Bianchini, C. Bohanna, M. A. Esteruelas, P Frediani, A. Meli, L. A. Oro, M. Peruzzini, Organometallics 1992, 11, 3837; c) M. A. Esteruelas, J. Herrero, A. M. Lopez, L. A. Oro, M. Schulz, H. Werner, Inorg. Chem. 1992, 31, 4013.
    • (1992) Inorg. Chem. , vol.31 , pp. 4013
    • Esteruelas, M.A.1    Herrero, J.2    Lopez, A.M.3    Oro, L.A.4    Schulz, M.5    Werner, H.6
  • 20
    • 0001588329 scopus 로고    scopus 로고
    • Reductions in Organic Chemistry
    • "Reductions in Organic Chemistry": M. Hudlicky, ACS Symp. Ser. 1996, 188.
    • (1996) ACS Symp. Ser. , vol.188
    • Hudlicky, M.1
  • 22
    • 0000429726 scopus 로고    scopus 로고
    • For examples, see a) M. Tanaka, Y. Watanabe, T. Mitsudo, Y. Yasunori, Y. Takegami, Chem. Lett. 1974, 137; b) R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499.
    • (1998) J. Org. Chem. , vol.63 , pp. 3499
    • Kuwano, R.1    Okuda, S.2    Ito, Y.3
  • 23
    • 0345599598 scopus 로고    scopus 로고
    • note
    • In the catalytic hydrogenation of trimethylsilyl enol ethers, the corresponding ketones are sometimes observed as by-products. This is explained by the reaction of trimethylsilyl enol ethers with adventitious water in the solvent.
  • 24
    • 0345599597 scopus 로고    scopus 로고
    • note
    • [13] Thus, in this novel reaction an enol product is initially produced, which isomerizes to the corresponding keto form.
  • 25
    • 0039602832 scopus 로고
    • A study on protonolysis of several silyl enol ethers showed that C-protonation occurred in the case of tert-butyldimethylsilyl enol ethers while no conclusion was made for trimethylsilyl enol ethers; M. H. Novice, H. R. Seikaly, A. D. Seiz, T. T. Tidwell, J. Am. Chem. Soc. 1980, 102, 5835.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5835
    • Novice, M.H.1    Seikaly, H.R.2    Seiz, A.D.3    Tidwell, T.T.4
  • 27
    • 0344737371 scopus 로고    scopus 로고
    • note
    • 6 was estimated to be 6.0.
  • 29
    • 0344737372 scopus 로고    scopus 로고
    • note
    • 6 was estimated to be 15.0.
  • 32
    • 0345167544 scopus 로고    scopus 로고
    • note
    • [12]
  • 34
    • 0000530876 scopus 로고    scopus 로고
    • b) C. Fehr, Angew. Chem. 1996, 108, 2726; Angew. Chem. Int. Ed. Engl. 1996, 35, 2566, and references therein.
    • (1996) Angew. Chem. , vol.108 , pp. 2726
    • Fehr, C.1
  • 35
    • 33751146774 scopus 로고    scopus 로고
    • and references therein
    • b) C. Fehr, Angew. Chem. 1996, 108, 2726; Angew. Chem. Int. Ed. Engl. 1996, 35, 2566, and references therein.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2566


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.