메뉴 건너뛰기




Volumn 129, Issue 1, 2007, Pages 22-23

Rh-catalyzed intermolecular reactions of alkynes with α-diazoesters that possess β-hydrogens: Ligand-based control over divergent pathways

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ALPHA DIAZOESTER DERIVATIVE; ESTER DERIVATIVE; HYDROGEN; LIGAND; RHENIUM; UNCLASSIFIED DRUG;

EID: 33846113394     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0660195     Document Type: Article
Times cited : (148)

References (36)
  • 8
    • 33846058196 scopus 로고    scopus 로고
    • Lead references to Rh-catalyzed alkyne insertion: (a) Padwa, A. J. Organomet. Chem. 2001, 617, 3.
    • Lead references to Rh-catalyzed alkyne insertion: (a) Padwa, A. J. Organomet. Chem. 2001, 617, 3.
  • 12
    • 33846104799 scopus 로고    scopus 로고
    • For an example of Rh-catalyred tandem intramolccular/intermolecular alkyne insertion, see ref 3d
    • (a) For an example of Rh-catalyred tandem intramolccular/intermolecular alkyne insertion, see ref 3d.
  • 13
    • 33846067519 scopus 로고    scopus 로고
    • Hoye has presented evidence that alkenyl carbenes may not be intermediates in intramolecular alkyne insertions. See ref 3c
    • (b) Hoye has presented evidence that alkenyl carbenes may not be intermediates in intramolecular alkyne insertions. See ref 3c.
  • 16
    • 0842266132 scopus 로고    scopus 로고
    • 4th ed, de Meijere, A, Ed, Georg Thieme Verlag: Stuttgart, Germany
    • (a) Baird, M. S. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1996; Vol. E17d, p 2695-2744.
    • (1996) Carbocyclic Three-Membered Ring Compounds , vol.E17d , pp. 2695-2744
    • Baird, M.S.1
  • 19
    • 0000913258 scopus 로고    scopus 로고
    • Lead references to catalytic cnantioselective cyclopropenations: (d) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
    • Lead references to catalytic cnantioselective cyclopropenations: (d) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
  • 24
    • 0001031980 scopus 로고    scopus 로고
    • For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references therein.
    • For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 and references therein.
  • 27
    • 0035929204 scopus 로고    scopus 로고
    • For use of the Cu-catalysts shown in Table 1 in cyclopropenation and cyclopropanation, see: (a) Diaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Chem. Commun. 2001, 1804.
    • For use of the Cu-catalysts shown in Table 1 in cyclopropenation and cyclopropanation, see: (a) Diaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Chem. Commun. 2001, 1804.
  • 29
    • 84987566668 scopus 로고    scopus 로고
    • For examples of Rh-catalyzed opening of cyclopropenes to putative akenylcarbene intermediates, see refs 3d and 8 and (a) Müller, P, Gränicher, C. Helv. Chim. Acta 1993, 76, 521
    • For examples of Rh-catalyzed opening of cyclopropenes to putative akenylcarbene intermediates, see refs 3d and 8 and (a) Müller, P.; Gränicher, C. Helv. Chim. Acta 1993, 76, 521.
  • 30
    • 33846050798 scopus 로고    scopus 로고
    • For examples of azulene and hydroazulene synthesis via intramolecular variants of the Büchner synthesis, see (a) Chapter 6 in ref 1
    • For examples of azulene and hydroazulene synthesis via intramolecular variants of the Büchner synthesis, see (a) Chapter 6 in ref 1.
  • 32
    • 2942567899 scopus 로고    scopus 로고
    • In studies that compared C-H insertion to β-hydride elimination, Rh2-(Piv)4 was slightly more selective than Rh2(Piv)4. In one example, 12b 85:15 selectivity was observed with Rh2(Piv)4 versus 78:22 with Rh2-(OAc)4. See: (a) Taber, D. F.; Joshi, P. V. J. Org. Chem. 2004, 69, 4276.
    • In studies that compared C-H insertion to β-hydride elimination, Rh2-(Piv)4 was slightly more selective than Rh2(Piv)4. In one example, 12b 85:15 selectivity was observed with Rh2(Piv)4 versus 78:22 with Rh2-(OAc)4. See: (a) Taber, D. F.; Joshi, P. V. J. Org. Chem. 2004, 69, 4276.
  • 34
    • 0028272257 scopus 로고    scopus 로고
    • In a study that compared O-H insertion to β-hydride elimination in the reaction of α-diazohydrocinnamate with water, Rh2(OAc)4 gave 82:18 selectvily for O-H insertion, whereas Rh2(9-adamantoate)4 gave 88:12 selectivity: Cox, G. G, Haigh, D, Hindley, R. M, Miller, D. J, Moody, C. J. Tetrahedron Lett. 1994, 35, 3139
    • In a study that compared O-H insertion to β-hydride elimination in the reaction of α-diazohydrocinnamate with water, Rh2(OAc)4 gave 82:18 selectvily for O-H insertion, whereas Rh2(9-adamantoate)4 gave 88:12 selectivity: Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139.
  • 35
    • 18244409381 scopus 로고    scopus 로고
    • For mechanistic proposals for intermolecular cyclopropenation that involve the direct reaction of the alkyne with a tetrabridged Rh-carbenoid via a concerted, asynchronous transition state, see refs 6d and 6c and (a) Nowlan, D. T, III; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190
    • For mechanistic proposals for intermolecular cyclopropenation that involve the direct reaction of the alkyne with a tetrabridged Rh-carbenoid via a concerted, asynchronous transition state, see refs 6d and 6c and (a) Nowlan, D. T., III; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190.
  • 36
    • 0025770242 scopus 로고    scopus 로고
    • For an alternate proposal in which ligand dissociation is thought to occur prior to cyclopropenation, see refs 6f and 6g. For mechanistic proposals in which ylide and alkenylcarbenes (analogous to 6 and 7) are considered as intermediates in intramolecular cyclopropenation, see ref 8b and (b) Padwa, A, Austin, D. J, Xu, S. E. Tetrahedron Lett. 1991, 32, 4103
    • For an alternate proposal in which ligand dissociation is thought to occur prior to cyclopropenation, see refs 6f and 6g. For mechanistic proposals in which ylide and alkenylcarbenes (analogous to 6 and 7) are considered as intermediates in intramolecular cyclopropenation, see ref 8b and (b) Padwa, A.; Austin, D. J.; Xu, S. E. Tetrahedron Lett. 1991, 32, 4103.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.