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Volumn 6, Issue 5, 2004, Pages 855-857

Synthesis of a new chiral nonracemic C2-symmetric 2,2′-bipyridyl ligand and its application in copper(I)-catalyzed enantioselective cyclopropanation reactions

Author keywords

[No Author keywords available]

Indexed keywords

2,2' BIPYRIDINE; ALKENE DERIVATIVE; COPPER COMPLEX; ESTER DERIVATIVE; LIGAND; PYRIDINE;

EID: 1642297206     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049853c     Document Type: Article
Times cited : (53)

References (30)
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    • For discussions on the coordination chemistry of 2,2́-bipyridines and 1,10-phenanthrolines, see: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 73-98. (b) Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73-98
    • Reedijk, J.1
  • 5
    • 0034299604 scopus 로고    scopus 로고
    • For discussions on the coordination chemistry of 2,2́-bipyridines and 1,10-phenanthrolines, see: (a) Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 73-98. (b) Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
    • (2000) Chem. Rev. , vol.100 , pp. 3553
    • Kaes, C.1    Katz, A.2    Hosseini, M.W.3
  • 6
    • 0033936085 scopus 로고    scopus 로고
    • For a recent review on chiral bis(oxazolines) in asymmetric transition metal catalyzed reactions, see for example: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 325
    • Johnson, J.S.1    Evans, D.A.2
  • 10
    • 0000114544 scopus 로고    scopus 로고
    • Supporting Information
    • On heating the acetate 4 with concentrated sulfuric acid for an extended period of time (1 h) the regioselectivity of this elimination reaction was compromised (9:1). Ruble and Fu have reported a related example in which a functionalized pyrindine is formed as a mixture of regioisomers (2:1): Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230 (Supporting Information).
    • (1996) J. Org. Chem. , vol.61 , pp. 7230
    • Ruble, J.C.1    Fu, G.C.2
  • 12
    • 1642414117 scopus 로고    scopus 로고
    • note
    • The enantioselectivity of this AD reaction was determined by analytical chiral HPLC (Daicel Chiracel OD column).
  • 13
    • 0343464590 scopus 로고    scopus 로고
    • 2-symmetric chiral ligand derived from (1R,2R)-trans-1,2- diaminocyclohexane in 80% ee (70% yield). However, the chiral ligand and osmium tetroxide are used stoichiometrically in this reaction; see: Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
    • (1999) J. Chem. Ed. , vol.76 , pp. 655
    • Spivey, A.C.1    Hanson, R.2    Scorah, N.3    Thorpe, S.J.4
  • 14
    • 0001532666 scopus 로고
    • 2-symmetric chiral ligand derived from (1R,2R)-trans-1,2- diaminocyclohexane in 80% ee (70% yield). However, the chiral ligand and osmium tetroxide are used stoichiometrically in this reaction; see: Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
    • (1993) J. Org. Chem. , vol.58 , pp. 1991
    • Hanessian, S.1    Meffre, P.2    Girard, M.3    Beaudoin, S.4    Sancéau, J.-Y.5    Bennani, Y.6
  • 15
    • 1642391512 scopus 로고    scopus 로고
    • note
    • Interestingly, the overall yield of the corresponding quinoline derivative of the acetal (+)-7 that has been prepared from cyclohexanone by the same procedures was significantly greater. However, the enantiomeric purity of this acetal was poor (∼5% ee).
  • 16
    • 0001213685 scopus 로고
    • 2PHAL using methanesulfonamide as an additive and 1 mol % of potassium osmate dihydrate: (a) Wang, Z.-M.; Kakiuchi, K., Sharpless, K. B. J. Org. Chem. 1994, 59, 6895. (b) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
    • (1994) J. Org. Chem. , vol.59 , pp. 6895
    • Wang, Z.-M.1    Kakiuchi, K.2    Sharpless, K.B.3
  • 17
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    • 2PHAL using methanesulfonamide as an additive and 1 mol % of potassium osmate dihydrate: (a) Wang, Z.-M.; Kakiuchi, K., Sharpless, K. B. J. Org. Chem. 1994, 59, 6895. (b) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7568
    • Wang, L.1    Sharpless, K.B.2
  • 24
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    • and references therein
    • The absolute stereochemistry of cyclopropane 10a was assigned as 1R,2R by comparison of the optical rotation with literature values; see for example: Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79 and references therein.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 79
    • Niimi, T.1    Uchida, T.2    Irie, R.3    Katsuki, T.4
  • 30
    • 1642363951 scopus 로고    scopus 로고
    • Ojima, I., Ed.; Wiley-VCH: New York, Chapter 5
    • Of note, disubstituted chiral bis(oxazoline) ligands provide improved enantioselection in AC reactions; see: Doyle, M. P. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 5.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed.
    • Doyle, M.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.