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Volumn 2, Issue 20, 2000, Pages 3047-3049

PINDY: A novel, pinene-derived bipyridine ligand and its application in asymmetric, copper(I)-catalyzed allylic oxidation

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EID: 0001153422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (107)

References (69)
  • 3
    • 0001827606 scopus 로고
    • Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Oxford
    • For the rich coordination chemistry of bipyridine and phenathroline, see, e.g.: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Oxford, 1987; Vol 2, p 73.
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73
    • Reedijk, J.1
  • 13
  • 36
    • 0043193156 scopus 로고    scopus 로고
    • PINene-Derived bipYridine
    • PINene-Derived bipYridine.
  • 39
    • 0041690228 scopus 로고
    • Identical with the known compound: (a) Hall, H. K. J. Org. Chem. 1963, 28, 3213.
    • (1963) J. Org. Chem. , vol.28 , pp. 3213
    • Hall, H.K.1
  • 43
    • 0043193154 scopus 로고    scopus 로고
    • note
    • 19 However, in view of the cost of the former and the difficulties associated with the availability of the latter reagent, none of them was particularly suitable for large-scale operations.
  • 47
    • 84978055185 scopus 로고
    • For the method of α-chloropyridine dimerization, see ref 6a and the following: (a) Dehmlow, E. V.; Sleegers, A. Liebigs Ann. Chem. 1992, 9, 953.
    • (1992) Liebigs Ann. Chem. , vol.9 , pp. 953
    • Dehmlow, E.V.1    Sleegers, A.2
  • 49
    • 0042190943 scopus 로고    scopus 로고
    • note
    • Although this coupling is, a priori, amenable to a catalytic process, reactions with sub-stoichiometric amounts (e.g., 10 mol %) of Ni(0) turned out to lead predominantly to the reduction product 7.
  • 51
    • 0042692077 scopus 로고    scopus 로고
    • note
    • 2) = 0.0973 for all data, Flack factor = 0.003(7). The estimated error in C-C bond lengths is in the range of 0.002-0.003 Å.
  • 52
    • 0033603853 scopus 로고    scopus 로고
    • For a similar distortion, see ref 9. Several oxazoline-type Cu(II) complexes have also been reported to exhibit distortion at Cu (although not to the extend observed for 8). For a recent summary, see: (a) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7559
    • Evans, D.A.1    Miller, S.J.2    Lectka, T.3    Von Matt, P.4
  • 63
    • 0042692052 scopus 로고    scopus 로고
    • note
    • 6.
  • 64
    • 0041690198 scopus 로고    scopus 로고
    • note
    • 3], its ultimate precursor 5 was found to be of 95% ee by HPLC.
  • 65
    • 0042190913 scopus 로고    scopus 로고
    • note
    • S = 13.8 min (major), UV detection at 220 nm.
  • 66
    • 0041690197 scopus 로고    scopus 로고
    • note
    • 26
  • 67
    • 0043193130 scopus 로고    scopus 로고
    • note
    • For the role of the counterion in Cu(I)- and Cu(II)-catalyzed reactions, see, e.g., ref 25.
  • 68
    • 0042692051 scopus 로고    scopus 로고
    • note
    • Apparently, the reaction requires a trace of water since adding molecular sieves resulted in a dramatic deceleration (though the enantioselectivity remained essentially unaffected).
  • 69
    • 0042692049 scopus 로고    scopus 로고
    • note
    • 26 have different "optimal substrates"; in the case of PINDY it is 11c that gives the highest enantioselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.