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Volumn 131, Issue 33, 2009, Pages 11640-11641

Enantioselective α-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ALDEHYDES; ARYLATION REACTIONS; ARYLATIONS; CHEMICAL EQUATIONS; ELECTRON-RICH AROMATICS; ENAMINES; ENANTIOSELECTIVE; ENANTIOSELECTIVE REACTIONS; HETEROCYCLES; OPEN-SHELL; ORTHO POSITION; PARA POSITION; RADICAL CATIONS; RADICAL MECHANISM; RADICAL SPECIES; SECONDARY AMINES; SELECTIVE OXIDATION; SINGLY OCCUPIED MOLECULAR ORBITALS;

EID: 69049104186     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9026902     Document Type: Article
Times cited : (229)

References (20)
  • 6
    • 33847307475 scopus 로고    scopus 로고
    • This racemization has been exploited for dynamic kinetic resolutions: Xie, J.-H, Zhou, Z.-T, Kong, W.-L, Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 1868
    • This racemization has been exploited for dynamic kinetic resolutions: Xie, J.-H.; Zhou, Z.-T.; Kong, W.-L.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 1868.
  • 7
    • 34547178180 scopus 로고    scopus 로고
    • With quinone Michael acceptors: (a) Alemán, J, Cabrera, S, Maerten, E, Overgaard, J, Jørgensen, K. A. Angew. Chem, Int. Ed. 2007, 46, 5520
    • With quinone Michael acceptors: (a) Alemán, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5520.
  • 12
    • 69049111539 scopus 로고    scopus 로고
    • Details of this work were described at the ACS Centennial Symposium: MacMillan, David W. C. Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008 (2008), ORGN-545. CODEN: 69KXQ2 AN 2008:954577 CAPLUS.
    • Details of this work were described at the ACS Centennial Symposium: MacMillan, David W. C. Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008 (2008), ORGN-545. CODEN: 69KXQ2 AN 2008:954577 CAPLUS.
  • 13
    • 1842661169 scopus 로고
    • For ortho-selective radical additions to anisole, see:, Abramovitch, R. A, Ed, Plenum Press: New York
    • For ortho-selective radical additions to anisole, see: Tiecco, M.; Testaferri, L. In Reactive Intermediates, Vol. 3; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; p 61.
    • (1983) Reactive Intermediates , vol.3 , pp. 61
    • Tiecco, M.1    Testaferri, L.2
  • 15
    • 70149099966 scopus 로고    scopus 로고
    • A correction for ref 8a was submitted on the same day as the original version of this manuscript (which also noted the mischaracterizations of ref 8a): J. Am. Chem. Soc. 2009, 131, 6640. While the authors of refs 8a and 8b did not provide experimental verification of the reassigned structures, our submission did so; see Supporting Information.
    • (b) A correction for ref 8a was submitted on the same day as the original version of this manuscript (which also noted the mischaracterizations of ref 8a): J. Am. Chem. Soc. 2009, 131, 6640. While the authors of refs 8a and 8b did not provide experimental verification of the reassigned structures, our submission did so; see Supporting Information.
  • 16
    • 69049100889 scopus 로고    scopus 로고
    • It should be noted that Nicolaou and co-workers observed para-selectivity with highly electron-rich 1,3,4-trisubstituted aryl rings see ref 8a
    • It should be noted that Nicolaou and co-workers observed para-selectivity with highly electron-rich 1,3,4-trisubstituted aryl rings (see ref 8a).
  • 17
    • 69049086411 scopus 로고    scopus 로고
    • An open-shell, radical pathway is also consistent with the successful addition of highly electron-deficient styrenes to radical cations such as 1 see ref 5d
    • An open-shell, radical pathway is also consistent with the successful addition of highly electron-deficient styrenes to radical cations such as 1 (see ref 5d).


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