One-pot sequential Pauson-Khand reaction - Transfer hydrogenation

Canadian Journal of Chemistry

Volumn 80, Issue 10, 2002, Pages 1327-1330

  Hätzelt, André ^a   Laschat, Sabine ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Pauson Khand reaction; Transfer hydrogenation

Indexed keywords

ACETYLENE; CATALYSIS; ISOMERS; KETONES; RUTHENIUM COMPOUNDS;

INDUCTION PERIOD;

HYDROGENATION;

ACETYLENE DERIVATIVE; BASE; KETONE; NORBORNENE DERIVATIVE; PHENYLACETYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; HYDROGENATION; PAUSON KHAND REACTION;

ZOOLOGY;

EID: 0036924989     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-172     Document Type: Article

References (45)

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13. Recent examples: (a) P. Eilbracht, C.L. Kranemann, and L. Bärfacker. Eur. J. Org. Chem. 1907 (1999); (b) T. Rische and P. Eilbracht. Tetrahedron, 54, 8441 (1998); (c) G. Dyker and P. Grundt. Helv. Chim. Acta, 82, 588 (1999); (d) D. Flubacher and G. Helmchen. Tetrahedron Lett. 40, 3867 (1999); (e) S. Cacchi, G. Fabrizi, and F. Marinelli. Synlett, 401 (1999); (f) C.-H. Jun, C.-W. Huch, and S.-J. Na. Angew. Chem. Int. Ed. 37, 145 (1998); (g) M. Thommen, L.A. Veretenov, R. Guidetti-Crept, and R. Keese. Helv. Chim. Acta, 79, 461 (1996); (h) J. Schoepfer, C. Marquis, C. Pasquier, and R. Neier. Chem. Commun. 1001 (1994); (i) P.G. Andersson and J.E. Bäckvall. J. Am. Chem. Soc. 114, 8696 (1992); (j) B.M. Trost and Y. Shi. J. Am. Chem. Soc. 113, 701 (1991).
14. Recent examples: (a) P. Eilbracht, C.L. Kranemann, and L. Bärfacker. Eur. J. Org. Chem. 1907 (1999); (b) T. Rische and P. Eilbracht. Tetrahedron, 54, 8441 (1998); (c) G. Dyker and P. Grundt. Helv. Chim. Acta, 82, 588 (1999); (d) D. Flubacher and G. Helmchen. Tetrahedron Lett. 40, 3867 (1999); (e) S. Cacchi, G. Fabrizi, and F. Marinelli. Synlett, 401 (1999); (f) C.-H. Jun, C.-W. Huch, and S.-J. Na. Angew. Chem. Int. Ed. 37, 145 (1998); (g) M. Thommen, L.A. Veretenov, R. Guidetti-Crept, and R. Keese. Helv. Chim. Acta, 79, 461 (1996); (h) J. Schoepfer, C. Marquis, C. Pasquier, and R. Neier. Chem. Commun. 1001 (1994); (i) P.G. Andersson and J.E. Bäckvall. J. Am. Chem. Soc. 114, 8696 (1992); (j) B.M. Trost and Y. Shi. J. Am. Chem. Soc. 113, 701 (1991).
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24. Reviews: (a) K.M. Brummond and J.L. Kent. Tetrahedron, 56, 1657 (2000); (b) Y.K. Chung. Coord. Chem. Rev. 188, 297 (1999); (c) O. Geis and H.-G. Schmalz. Angew. Chem. Int. Ed. 37, 911 (1998); (d) N. Jeong. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Edited by C. Bolm and M. Beller. Wiley-VCH, New York. 1998. p. 560; (e) N.E. Schore. In Comprehensive Organometallic Chemistry II: A Review of the Literature 1982-1994. Vol. 12. Edited by E.W. Abel, F.G.A. Stone, and G. Wilkinson. Pergamon Press, Oxford. 1995. p. 703; (f) N.E. Schore. Org. React. 40, 1 (1991); (g) N.E. Schore. In Comprehensive organic synthesis: Selectivity, strategy, & efficiency in modern organic chemistry. Vol. 5. Edited by B.M. Trost. Pergamon Press, Oxford. 1991. p. 1037; (h) P.L. Pauson. Tetrahedron, 41, 5855 (1985); (i) For a sequence of Pauson-Khand reaction and photochemical rearrangement see: I. Marchueta, S. Olivella, L. Sola, A. Moyano, M.A. Pericas, and A. Riera. Org. Lett. 3, 3197 (2001).
25. Reviews: (a) K.M. Brummond and J.L. Kent. Tetrahedron, 56, 1657 (2000); (b) Y.K. Chung. Coord. Chem. Rev. 188, 297 (1999); (c) O. Geis and H.-G. Schmalz. Angew. Chem. Int. Ed. 37, 911 (1998); (d) N. Jeong. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Edited by C. Bolm and M. Beller. Wiley-VCH, New York. 1998. p. 560; (e) N.E. Schore. In Comprehensive Organometallic Chemistry II: A Review of the Literature 1982-1994. Vol. 12. Edited by E.W. Abel, F.G.A. Stone, and G. Wilkinson. Pergamon Press, Oxford. 1995. p. 703; (f) N.E. Schore. Org. React. 40, 1 (1991); (g) N.E. Schore. In Comprehensive organic synthesis: Selectivity, strategy, & efficiency in modern organic chemistry. Vol. 5. Edited by B.M. Trost. Pergamon Press, Oxford. 1991. p. 1037; (h) P.L. Pauson. Tetrahedron, 41, 5855 (1985); (i) For a sequence of Pauson-Khand reaction and photochemical rearrangement see: I. Marchueta, S. Olivella, L. Sola, A. Moyano, M.A. Pericas, and A. Riera. Org. Lett. 3, 3197 (2001).
26. Reviews: (a) K.M. Brummond and J.L. Kent. Tetrahedron, 56, 1657 (2000); (b) Y.K. Chung. Coord. Chem. Rev. 188, 297 (1999); (c) O. Geis and H.-G. Schmalz. Angew. Chem. Int. Ed. 37, 911 (1998); (d) N. Jeong. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Edited by C. Bolm and M. Beller. Wiley-VCH, New York. 1998. p. 560; (e) N.E. Schore. In Comprehensive Organometallic Chemistry II: A Review of the Literature 1982-1994. Vol. 12. Edited by E.W. Abel, F.G.A. Stone, and G. Wilkinson. Pergamon Press, Oxford. 1995. p. 703; (f) N.E. Schore. Org. React. 40, 1 (1991); (g) N.E. Schore. In Comprehensive organic synthesis: Selectivity, strategy, & efficiency in modern organic chemistry. Vol. 5. Edited by B.M. Trost. Pergamon Press, Oxford. 1991. p. 1037; (h) P.L. Pauson. Tetrahedron, 41, 5855 (1985); (i) For a sequence of Pauson-Khand reaction and photochemical rearrangement see: I. Marchueta, S. Olivella, L. Sola, A. Moyano, M.A. Pericas, and A. Riera. Org. Lett. 3, 3197 (2001).
27. Reviews: (a) K.M. Brummond and J.L. Kent. Tetrahedron, 56, 1657 (2000); (b) Y.K. Chung. Coord. Chem. Rev. 188, 297 (1999); (c) O. Geis and H.-G. Schmalz. Angew. Chem. Int. Ed. 37, 911 (1998); (d) N. Jeong. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Edited by C. Bolm and M. Beller. Wiley-VCH, New York. 1998. p. 560; (e) N.E. Schore. In Comprehensive Organometallic Chemistry II: A Review of the Literature 1982-1994. Vol. 12. Edited by E.W. Abel, F.G.A. Stone, and G. Wilkinson. Pergamon Press, Oxford. 1995. p. 703; (f) N.E. Schore. Org. React. 40, 1 (1991); (g) N.E. Schore. In Comprehensive organic synthesis: Selectivity, strategy, & efficiency in modern organic chemistry. Vol. 5. Edited by B.M. Trost. Pergamon Press, Oxford. 1991. p. 1037; (h) P.L. Pauson. Tetrahedron, 41, 5855 (1985); (i) For a sequence of Pauson-Khand reaction and photochemical rearrangement see: I. Marchueta, S. Olivella, L. Sola, A. Moyano, M.A. Pericas, and A. Riera. Org. Lett. 3, 3197 (2001).
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30. Reviews: (a) S. Gladiali and G. Mestroni. In Transition Metals for Organic Synthesis. Vol. 2. Edited by C. Bolm and M. Beller. Wiley-VCH, Weinheim. 1999. p. 97; (b) T. Naota, H. Takaya, and S.-I. Murahashi. Chem. Rev. 98, 2599 (1998); (c) R. Noyori and S. Hashiguchi. Acc. Chem. Res. 30, 97 (1997); (d) G. Zassinovich, G. Mestroni, and S. Gladiali. Chem. Rev. 92, 1051 (1992); (e) J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G.-Z. Wang. In Perspective in Coordination Chemistry. Edited by A.F. Williams, C. Floriani, and A. E. Merbach. Verlag Helvetica Chimica Acta, Basel. 1992. p. 463; (f) R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle. Chem. Rev. 85, 129 (1985); (g) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, and S.J. Gladiali. J. Mol. Catal. 12, 265 (1981).
31. Reviews: (a) S. Gladiali and G. Mestroni. In Transition Metals for Organic Synthesis. Vol. 2. Edited by C. Bolm and M. Beller. Wiley-VCH, Weinheim. 1999. p. 97; (b) T. Naota, H. Takaya, and S.-I. Murahashi. Chem. Rev. 98, 2599 (1998); (c) R. Noyori and S. Hashiguchi. Acc. Chem. Res. 30, 97 (1997); (d) G. Zassinovich, G. Mestroni, and S. Gladiali. Chem. Rev. 92, 1051 (1992); (e) J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G.-Z. Wang. In Perspective in Coordination Chemistry. Edited by A.F. Williams, C. Floriani, and A. E. Merbach. Verlag Helvetica Chimica Acta, Basel. 1992. p. 463; (f) R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle. Chem. Rev. 85, 129 (1985); (g) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, and S.J. Gladiali. J. Mol. Catal. 12, 265 (1981).
32. Reviews: (a) S. Gladiali and G. Mestroni. In Transition Metals for Organic Synthesis. Vol. 2. Edited by C. Bolm and M. Beller. Wiley-VCH, Weinheim. 1999. p. 97; (b) T. Naota, H. Takaya, and S.-I. Murahashi. Chem. Rev. 98, 2599 (1998); (c) R. Noyori and S. Hashiguchi. Acc. Chem. Res. 30, 97 (1997); (d) G. Zassinovich, G. Mestroni, and S. Gladiali. Chem. Rev. 92, 1051 (1992); (e) J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G.-Z. Wang. In Perspective in Coordination Chemistry. Edited by A.F. Williams, C. Floriani, and A. E. Merbach. Verlag Helvetica Chimica Acta, Basel. 1992. p. 463; (f) R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle. Chem. Rev. 85, 129 (1985); (g) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, and S.J. Gladiali. J. Mol. Catal. 12, 265 (1981).
33. Reviews: (a) S. Gladiali and G. Mestroni. In Transition Metals for Organic Synthesis. Vol. 2. Edited by C. Bolm and M. Beller. Wiley-VCH, Weinheim. 1999. p. 97; (b) T. Naota, H. Takaya, and S.-I. Murahashi. Chem. Rev. 98, 2599 (1998); (c) R. Noyori and S. Hashiguchi. Acc. Chem. Res. 30, 97 (1997); (d) G. Zassinovich, G. Mestroni, and S. Gladiali. Chem. Rev. 92, 1051 (1992); (e) J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G.-Z. Wang. In Perspective in Coordination Chemistry. Edited by A.F. Williams, C. Floriani, and A. E. Merbach. Verlag Helvetica Chimica Acta, Basel. 1992. p. 463; (f) R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle. Chem. Rev. 85, 129 (1985); (g) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, and S.J. Gladiali. J. Mol. Catal. 12, 265 (1981).
34. Reviews: (a) S. Gladiali and G. Mestroni. In Transition Metals for Organic Synthesis. Vol. 2. Edited by C. Bolm and M. Beller. Wiley-VCH, Weinheim. 1999. p. 97; (b) T. Naota, H. Takaya, and S.-I. Murahashi. Chem. Rev. 98, 2599 (1998); (c) R. Noyori and S. Hashiguchi. Acc. Chem. Res. 30, 97 (1997); (d) G. Zassinovich, G. Mestroni, and S. Gladiali. Chem. Rev. 92, 1051 (1992); (e) J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G.-Z. Wang. In Perspective in Coordination Chemistry. Edited by A.F. Williams, C. Floriani, and A. E. Merbach. Verlag Helvetica Chimica Acta, Basel. 1992. p. 463; (f) R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle. Chem. Rev. 85, 129 (1985); (g) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, and S.J. Gladiali. J. Mol. Catal. 12, 265 (1981).
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