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Volumn 67, Issue 21, 2002, Pages 7446-7450

Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

EID: 0037131281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0262661     Document Type: Article
Times cited : (138)

References (41)
  • 1
    • 0001136410 scopus 로고
    • Hegedus, L.S., Ed.; Pergamon: Oxford, UK
    • Recent reviews of the Pauson-Khand-type) reaction: Schore, N. E. (a) In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 703-739. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911-914. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, pp 560-577.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703-739
    • Schore, N.E.1
  • 2
    • 0031971911 scopus 로고    scopus 로고
    • Recent reviews of the Pauson-Khand-type) reaction: Schore, N. E. (a) In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 703-739. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911-914. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, pp 560-577.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 911-914
    • Geis, O.1    Schmalz, H.G.2
  • 3
    • 0000213863 scopus 로고    scopus 로고
    • Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany
    • Recent reviews of the Pauson-Khand-type) reaction: Schore, N. E. (a) In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 703-739. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911-914. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, pp 560-577.
    • (1998) Transition Metals In Organic Synthesis , vol.1 , pp. 560-577
    • Jeong, N.1
  • 28
    • 0011047205 scopus 로고
    • Colquhoun, H.M., Thompson, D.J., Twigg, M.V., Eds.; Plenum, New York: Chapter 11
    • (c) Jardine, F. H. In Carbonylations; Colquhoun, H. M., Thompson, D. J., Twigg, M. V., Eds.; Plenum: New York, 1991; Chapter 11, pp 407-469.
    • (1991) Carbonylations , pp. 407-469
    • Jardine, F.H.1
  • 33
    • 0035849442 scopus 로고    scopus 로고
    • and references therein
    • Decarbonylated CO from formic acid is utilized in metal-catalyzed hydroxycarbonylation: Simonato, J.-P.; Walter, T.; Métivier, P. J. Mol. Catal. A 2001, 171, 91-94 and references therein.
    • (2001) J. Mol. Catal. A , vol.171 , pp. 91-94
    • Simonato, J.-P.1    Walter, T.2    Métivier, P.3
  • 35
    • 0037123291 scopus 로고    scopus 로고
    • Independently, Pauson-Khand-type reaction with pentafluorobenzaldehyde as a CO source in xylene was reported, see: Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806-3807.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3806-3807
    • Morimoto, T.1    Fuji, K.2    Tsutsumi, K.3    Kakiuchi, K.4
  • 36
    • 2142727845 scopus 로고    scopus 로고
    • note
    • A reaction mechanism with one catalytic cycle is also possible, where metal carbonyl complex A itself acts as a catalyst for carbonylative coupling. But this mechanism conflicts with highly enantioselective induction by chiral diphosphine (Table 6), since the dissociation of phosphine ligand from the metal center is needed for coordination of an enyne, which is an enantiomerically differentiated step.
  • 37
    • 0034700573 scopus 로고    scopus 로고
    • A recent example of solvent-free enantioselective reaction with organometallic compounds: Sato, I.; Saito, T.; Soai, K. Chem. Commun. 2000, 2471-2472.
    • (2000) Chem. Commun. , pp. 2471-2472
    • Sato, I.1    Saito, T.2    Soai, K.3
  • 38
    • 2142667491 scopus 로고    scopus 로고
    • note
    • From the sign of optical rotation, the absolute configuration of obtained 2a proved to be S (ref 3b). This means that the mechanism of asymmetric induction with aldehyde as a CO source by the Rh-tolBINAP system is the same as that with CO gas (refs 7 and 8).


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