메뉴 건너뛰기




Volumn , Issue 1, 2010, Pages 19-32

The diene effect: The design, development, and Mechanistic investigation of metal-catalyzed diene-yne, diene-ene, and diene-allene [2+2+1] cycloaddition reactions

Author keywords

Allenes; Cycloaddition; Heterogeneous catalysis; Pauson khand reaction; Rhodium

Indexed keywords


EID: 73349099334     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900929     Document Type: Article
Times cited : (58)

References (101)
  • 8
    • 34447094656 scopus 로고    scopus 로고
    • For a thematic issue on green chemistry, see
    • a) For a thematic issue on green chemistry, see: Chem. Rev. 2007, 107, 2167-2820;
    • (2007) Chem. Rev , vol.107 , pp. 2167-2820
  • 9
    • 0003980673 scopus 로고    scopus 로고
    • For the principles of green chemistry, see:, Oxford University Press, New York
    • For the principles of green chemistry, see: P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998, p. 30;
    • (1998) Green Chemistry: Theory and Practice , pp. 30
    • Anastas, P.T.1    Warner, J.C.2
  • 10
    • 73349120413 scopus 로고    scopus 로고
    • For more information, visit the ACS Green Chemistry Institute at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html? DOC= greenchemistryinstitute\index.html.
    • For more information, visit the ACS Green Chemistry Institute at http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html? DOC= greenchemistryinstitute\index.html.
  • 11
  • 12
    • 51649130191 scopus 로고    scopus 로고
    • and For recent and seminal discussions of atom economy, see
    • a) For recent and seminal discussions of atom economy, see: C.-J. Li, B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13197-13202 and
    • (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 13197-13202
    • Li, C.-J.1    Trost, B.M.2
  • 13
    • 0026418434 scopus 로고
    • B. M. Trost, Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 15
    • 0028956752 scopus 로고    scopus 로고
    • For the first [5+2] reaction of a VCP, see: P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721;
    • a) For the first [5+2] reaction of a VCP, see: P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721;
  • 16
    • 0032576188 scopus 로고    scopus 로고
    • For the first intermolecular [5+2] reaction, see: P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998, 120, 10976-10977;
    • For the first intermolecular [5+2] reaction, see: P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998, 120, 10976-10977;
  • 17
    • 0032543523 scopus 로고    scopus 로고
    • For the first [5+2] reaction with an alkene, see: P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, N. Pleuss, Tetrahedron 1998, 54, 7203-7220;
    • For the first [5+2] reaction with an alkene, see: P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, N. Pleuss, Tetrahedron 1998, 54, 7203-7220;
  • 18
    • 0033538287 scopus 로고    scopus 로고
    • For the first [5+2] reaction with allenes, see: P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
    • For the first [5+2] reaction with allenes, see: P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
  • 19
    • 18644375951 scopus 로고    scopus 로고
    • For the first intermolecular [5+2] reaction with allenes, see: H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531;
    • For the first intermolecular [5+2] reaction with allenes, see: H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531;
  • 20
    • 0037176267 scopus 로고    scopus 로고
    • For the first [5+2] reaction with cyclopropyl imines, see: P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154-15155.
    • For the first [5+2] reaction with cyclopropyl imines, see: P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154-15155.
  • 27
    • 3342979429 scopus 로고    scopus 로고
    • For computational analysis of the mechanism of the [5+2] reaction using density functional theory, see: Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154-9155.
    • For computational analysis of the mechanism of the [5+2] reaction using density functional theory, see: Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154-9155.
  • 29
    • 33746278459 scopus 로고    scopus 로고
    • For a [6+1] reaction allenylcyclobutanes, see: P. A. Wender, N. M. Deschamps, R. Sun, Angew. Chem. Int. Ed. 2006, 45, 3957-3960;
    • a) For a [6+1] reaction allenylcyclobutanes, see: P. A. Wender, N. M. Deschamps, R. Sun, Angew. Chem. Int. Ed. 2006, 45, 3957-3960;
  • 30
    • 29244440374 scopus 로고    scopus 로고
    • For the carbonylative rearrangement of allenic ethers, see
    • For the carbonylative rearrangement of allenic ethers, see: P. A. Wender, N. M. Deschamps, R. Sun, Can. J. Chem. 2005, 83, 838-842.
    • (2005) Can. J. Chem , vol.83 , pp. 838-842
    • Wender, P.A.1    Deschamps, N.M.2    Sun, R.3
  • 36
    • 0001230097 scopus 로고
    • For related subsequent reports by Livinghouse and Wender using alkenes and allenes, see: b
    • For related subsequent reports by Livinghouse and Wender using alkenes and allenes, see: b) R. S. Jolly, G. Luedtke, D. Sheehan, T. Livinghouse, J. Am. Chem. Soc. 1990, 112, 4965-4966;
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 4965-4966
    • Jolly, R.S.1    Luedtke, G.2    Sheehan, D.3    Livinghouse, T.4
  • 38
    • 73349117650 scopus 로고    scopus 로고
    • For the trapping of intermediates in the [4+2] reaction with an alkyne to achieve a [4+2+2] reaction, see: P. A. Wender, J. P. Christy, J. Am. Chem. Soc. 2006, 128, 6530-6531.
    • For the trapping of intermediates in the [4+2] reaction with an alkyne to achieve a [4+2+2] reaction, see: P. A. Wender, J. P. Christy, J. Am. Chem. Soc. 2006, 128, 6530-6531.
  • 39
    • 0037693723 scopus 로고    scopus 로고
    • For the intramolecular diene-yne [4+2+1] and [2+2+1] reactions, see P. A. Wender, N. M. Deschamps, G. G. Gamber, Angew. Chem. Int. Ed. 2003, 42, 1853-1857;
    • a) For the intramolecular diene-yne [4+2+1] and [2+2+1] reactions, see P. A. Wender, N. M. Deschamps, G. G. Gamber, Angew. Chem. Int. Ed. 2003, 42, 1853-1857;
  • 40
    • 4143064955 scopus 로고    scopus 로고
    • For the intermolecular dienyl-Pauson-Khand reaction, see
    • For the intermolecular dienyl-Pauson-Khand reaction, see: P. A. Wender, N. M. Deschamps, T. J. Williams, Angew. Chem. Int. Ed. 2004, 43, 3076-3079;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3076-3079
    • Wender, P.A.1    Deschamps, N.M.2    Williams, T.J.3
  • 41
    • 2442555184 scopus 로고    scopus 로고
    • For the diene-ene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, J. Am. Chem. Soc. 2004, 126, 5948-5949;
    • For the diene-ene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, J. Am. Chem. Soc. 2004, 126, 5948-5949;
  • 42
    • 33746304119 scopus 로고    scopus 로고
    • For the diene-allene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, Angew. Chem. Int. Ed. 2006, 45, 2459-2462.
    • For the diene-allene [2+2+1] reaction, see: P. A. Wender, M. P. Croatt, N. M. Deschamps, Angew. Chem. Int. Ed. 2006, 45, 2459-2462.
  • 43
    • 33845245890 scopus 로고    scopus 로고
    • For recent reviews including work from the groups of Brummond, Buchwald, Carretero, Chung, Cook, Greene, Jeong, Krafft, Livinghouse, Mitsudo, Murai, Mukai, Narasaka, Periás, Periasamy, Schore, Rautenstrauch, and Yamaguchi, see: a
    • For recent reviews including work from the groups of Brummond, Buchwald, Carretero, Chung, Cook, Greene, Jeong, Krafft, Livinghouse, Mitsudo, Murai, Mukai, Narasaka, Periás, Periasamy, Schore, Rautenstrauch, and Yamaguchi, see: a) T. Shibata, Adv. Synth. Catal. 2006, 348, 2328-2336;
    • (2006) Adv. Synth. Catal , vol.348 , pp. 2328-2336
    • Shibata, T.1
  • 50
    • 73349128575 scopus 로고    scopus 로고
    • Albany Molecular Research Inc
    • Technical Report No. 18, 4, New York
    • L. Yet, Technical Report No. 18, Vol 4, Albany Molecular Research Inc., New York, 2000.
    • (2000)
    • Yet, L.1
  • 51
    • 0013265679 scopus 로고    scopus 로고
    • For an example using a stoichiometric organometallic reagent as one of the components in a [4+2+1] reaction, see: J. W. Herndon, G. Chatterjee, P. P. Patel, J. J. Matsi, S. U. Turner, J. J. Harp, M. D. Reid, J. Am. Chem. Soc. 1991, 113, 7808-7809;
    • a) For an example using a stoichiometric organometallic reagent as one of the components in a [4+2+1] reaction, see: J. W. Herndon, G. Chatterjee, P. P. Patel, J. J. Matsi, S. U. Turner, J. J. Harp, M. D. Reid, J. Am. Chem. Soc. 1991, 113, 7808-7809;
  • 52
    • 4544342224 scopus 로고    scopus 로고
    • For a metal-catalyzed [4+2+1] reaction of a diene-yne and trimethylsilyldiazomethane subsequently reported, see: J. Montgomery, Y. Ni, J. Am. Chem. Soc. 2004, 126, 11162-11163.
    • For a metal-catalyzed [4+2+1] reaction of a diene-yne and trimethylsilyldiazomethane subsequently reported, see: J. Montgomery, Y. Ni, J. Am. Chem. Soc. 2004, 126, 11162-11163.
  • 55
    • 73349094529 scopus 로고    scopus 로고
    • For an initially reported [3+2+1] reaction that was corrected to be a diene-ene [2+2+1] reaction, see: Y. K. Chung, S. I. Lee, J. H. Park, S.-G. Lee, J. Am. Chem. Soc. 2004, 126, 10190
    • For an initially reported [3+2+1] reaction that was corrected to be a diene-ene [2+2+1] reaction, see: Y. K. Chung, S. I. Lee, J. H. Park, S.-G. Lee, J. Am. Chem. Soc. 2004, 126, 10190
  • 56
    • 1542287652 scopus 로고    scopus 로고
    • [J. Am. Chem. Soc. 2004, 126, 2714-2715].
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 2714-2715
  • 58
    • 0034638410 scopus 로고    scopus 로고
    • For a report of an enantioselective intermolecular Pauson-Khand reaction, see
    • For a report of an enantioselective intermolecular Pauson-Khand reaction, see: T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852-9853;
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 9852-9853
    • Shibata, T.1    Takagi, K.2
  • 59
    • 18844403627 scopus 로고    scopus 로고
    • For a review of components in the intermolecular Pauson-Khand reaction, see
    • For a review of components in the intermolecular Pauson-Khand reaction, see: S. E. Gibson, N. Mainolfi, Angew. Chem. Int. Ed. 2005, 44, 3022-3037.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3022-3037
    • Gibson, S.E.1    Mainolfi, N.2
  • 60
    • 0001383865 scopus 로고
    • For a seminal contribution, see
    • a) For a seminal contribution, see: M. E. Krafft, J. Am. Chem. Soc. 1988, 110, 968-970;
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 968-970
    • Krafft, M.E.1
  • 66
    • 73349124331 scopus 로고    scopus 로고
    • The authors report trans-fusion of the rings of 50 based on NOESY crosspeaks; however, the spectroscopic data for 50 match those of 55, which appears to have cis-fusion of the rings based on strong 1D nOe enhancement between the two angular hydrogen atoms. Importantly, the diastereotopic methyl peaks from the malonate tether in 49 appear as a 6-hydrogen singlet in the 1H NMR spectrum although the 1H NMR spectrum of 50 and all analogous products formed from the diene-ene [2+2+1] reaction with a malonate tether have significant separation of the two methyl peaks. Based on this data, it appears that 50 is incorrectly assigned and is actually cis-fused and that 49 is correctly assigned as the trans-fused bicycle.
    • The authors report trans-fusion of the rings of 50 based on NOESY crosspeaks; however, the spectroscopic data for 50 match those of 55, which appears to have cis-fusion of the rings based on strong 1D nOe enhancement between the two angular hydrogen atoms. Importantly, the diastereotopic methyl peaks from the malonate tether in 49 appear as a 6-hydrogen singlet in the 1H NMR spectrum although the 1H NMR spectrum of 50 and all analogous products formed from the diene-ene [2+2+1] reaction with a malonate tether have significant separation of the two methyl peaks. Based on this data, it appears that 50 is incorrectly assigned and is actually cis-fused and that 49 is correctly assigned as the trans-fused bicycle.
  • 71
    • 73349093234 scopus 로고    scopus 로고
    • WO 02053517, EP 1355872, US 680922;
    • R. M. Moriarty, H. Batra, WO 02053517, EP 1355872, US 680922;
    • Moriarty, R.M.1    Batra, H.2
  • 73
    • 73349091682 scopus 로고    scopus 로고
    • It should be noted that in ref.[32b, 10 mol, catalyst was reported to have a 73% yield on the gram-scale, but ref.[32a] was run with stoichiometric catalyst loading on a 4.9 kilogram scale
    • [32a] was run with stoichiometric catalyst loading on a 4.9 kilogram scale.
  • 74
    • 73349084122 scopus 로고    scopus 로고
    • For a review of the allenic Pauson-Khand reaction including significant contributions from the groups of Brummond, Cazes, Livinghouse, Alcaide, Mukai, Cook, and Shibata, see: B. Alcaide, P. Almendros, Chem. 2004, 3377-3383
    • For a review of the allenic Pauson-Khand reaction including significant contributions from the groups of Brummond, Cazes, Livinghouse, Alcaide, Mukai, Cook, and Shibata, see: B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2004, 3377-3383.
  • 75
    • 33751397119 scopus 로고    scopus 로고
    • I- catalyzed allenic Pauson-Khand reaction based on DFT calculations, see: A. S. Bayden, K. M. Brummond, K. D. Jordan, Organometallics 2006, 25, 5204-5206.
    • I- catalyzed allenic Pauson-Khand reaction based on DFT calculations, see: A. S. Bayden, K. M. Brummond, K. D. Jordan, Organometallics 2006, 25, 5204-5206.
  • 76
    • 33646353039 scopus 로고    scopus 로고
    • For the first [2+2+1] reaction of a sulfonyl allene and an alkene, see: F. Inagaki, C. Mukai, Org. Lett. 2006, 8, 1217-1220;
    • a) For the first [2+2+1] reaction of a sulfonyl allene and an alkene, see: F. Inagaki, C. Mukai, Org. Lett. 2006, 8, 1217-1220;
  • 77
    • 61849097162 scopus 로고    scopus 로고
    • For a recent [2+2+1] reaction of sulfonyl allenes with a tethered allene, see: F. Inagaki, S. Narita, T. Hasegawa, S. Kitagaki, C. Mukai, Angew. Chem. Int. Ed. 2009, 48, 2007-2011.
    • For a recent [2+2+1] reaction of sulfonyl allenes with a tethered allene, see: F. Inagaki, S. Narita, T. Hasegawa, S. Kitagaki, C. Mukai, Angew. Chem. Int. Ed. 2009, 48, 2007-2011.
  • 80
    • 34548711324 scopus 로고    scopus 로고
    • For examples of a diene acting as a two-carbon component but accelerating the reaction relative to an isolated alkene, see: M. Gulías, J. Durán, F. López, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2007, 129, 11026-11027;
    • a) For examples of a diene acting as a two-carbon component but accelerating the reaction relative to an isolated alkene, see: M. Gulías, J. Durán, F. López, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2007, 129, 11026-11027;
  • 82
    • 42649096946 scopus 로고    scopus 로고
    • For a recent report which examined the mechanism of the diene-ene [2+2+1] reaction with DFT calculations, see: W. H. Pitcock Jr, R. L. Lord, M.-H. Baik, J. Am. Chem. Soc. 2008, 130, 5821-5830.
    • For a recent report which examined the mechanism of the diene-ene [2+2+1] reaction with DFT calculations, see: W. H. Pitcock Jr, R. L. Lord, M.-H. Baik, J. Am. Chem. Soc. 2008, 130, 5821-5830.
  • 83
    • 73349084785 scopus 로고    scopus 로고
    • This step would additionally involve conversion of the dimeric rhodium catalyst into two monomeric rhodium catalysts. This is presumably facile in the presence of dienes
    • This step would additionally involve conversion of the dimeric rhodium catalyst into two monomeric rhodium catalysts. This is presumably facile in the presence of dienes.
  • 84
    • 73349144100 scopus 로고    scopus 로고
    • This structure could be an intermediate or the transition state between two intermediates with rhodium coordinated to either the alpha or beta face of the alkene
    • This structure could be an intermediate or the transition state between two intermediates with rhodium coordinated to either the alpha or beta face of the alkene.
  • 87
    • 73349118614 scopus 로고    scopus 로고
    • The intramolecular dienyl-Pauson-Khand reaction was explored mostly using a different catalyst system, RhCl (CO, PPh3) 2/ AgSbF6, but to compare all of the reactions of dienes tethered to π-systems, a single catalyst system was chosen to study, RhCl (CO) 2]2
    • 2.
  • 88
    • 0035809284 scopus 로고    scopus 로고
    • 13C NMR and Rh-C coupling constants, see: a S. C. van der Slot, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Iggo, B. T. Heaton, Organometallics 2001, 20, 430-441;
    • 13C NMR and Rh-C coupling constants, see: a) S. C. van der Slot, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Iggo, B. T. Heaton, Organometallics 2001, 20, 430-441;
  • 96
    • 0037205927 scopus 로고    scopus 로고
    • [J. Am. Chem. Soc. 2002, 124, 8782-8783];
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 8782-8783
  • 100
    • 73349104247 scopus 로고    scopus 로고
    • Ref.[18];
    • [18];


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.