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Volumn 11, Issue 24, 2009, Pages 5682-5685

Brucine-derived amino alcohol catalyzed asymmetric Henry reaction: An orthogonal enantioselectivity approach

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EID: 72849133517     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902380z     Document Type: Article
Times cited : (95)

References (61)
  • 1
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    • Yamamoto, H., Ishihara, K., Eds.; Wiley-VCH: Weinheim
    • Acid Catalysis in Modern Organic Synthesis; Yamamoto, H., Ishihara, K., Eds.; Wiley-VCH: Weinheim, 2008.
    • (2008) Acid Catalysis in Modern Organic Synthesis
  • 12
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany
    • For recent reviews, see: (a) Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vol. III, pp 1075-1090.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1075-1090
    • Shibasaki, M.1    Gröger, H.2
  • 48
    • 7444242815 scopus 로고    scopus 로고
    • Using α-keto esters and nitromethane, Henry products with less than 60% ee were obtained from Cu(II)/bis(thiazoline) catalysis; see: (a) Lu, S.-F.; Du, D.-M.; Zhang, S.-W.; Xu, J. Tetrahedron: Asymmetry 2004, 15, 3433.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3433
    • Lu, S.-F.1    Du, D.-M.2    Zhang, S.-W.3    Xu, J.4
  • 49
    • 17744381382 scopus 로고    scopus 로고
    • Enantiomeric Henry products were observed in the Et2Zn catalysis in the range of 13-85% ee; see: (b) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712.
    • (2005) J. Org. Chem. , vol.70 , pp. 3712
    • Du, D.-M.1    Lu, S.-F.2    Fang, T.3    Xu, J.4
  • 50
    • 72849146841 scopus 로고    scopus 로고
    • see: (c) ref lie
    • 2Zn and 8 mol % of chiral bisoxazolidine; see: (c) ref lie.
  • 51
    • 70349907587 scopus 로고    scopus 로고
    • Reversal of enantioselectivity was observed in the Cu(I) catalysis in the range of 74-97% ee; see: (d) Spangler, K. Y.; Wolf, C. Org. Lett. 2009, 11, 4724.
    • (2009) Org. Lett. , vol.11 , pp. 4724
    • Spangler, K.Y.1    Wolf, C.2
  • 52
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    • 2 (0% ee)
    • 2 (0% ee).
  • 53
    • 72849130671 scopus 로고    scopus 로고
    • Use of 2-Me-THF at -15 °C resulted in the partial suspension of CuOAc/1 catalyst. Use of 5 mol % of catalyst loading gave (5)-4a in 75% yield and 83% ee
    • Use of 2-Me-THF at -15 °C resulted in the partial suspension of CuOAc/1 catalyst. Use of 5 mol % of catalyst loading gave (5)-4a in 75% yield and 83% ee.
  • 54
    • 72849152875 scopus 로고    scopus 로고
    • 2Zn in toluene at 0 °C gave 40% ee and 54% ee, respectively
    • 2Zn in toluene at 0 °C gave 40% ee and 54% ee, respectively.
  • 56
    • 72849111016 scopus 로고    scopus 로고
    • See also ref 17c
    • (b)See also ref 17c.
  • 57
    • 72849123165 scopus 로고
    • For recent contributions, see refs 16 and 17 and references cited therein
    • For two mechanistic models, see: (a) Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1101. For recent contributions, see refs 16 and 17 and references cited therein.
    • (1982) . Chim. Acta , vol.65 , pp. 1101
    • Seebach, D.1    Beck, A.K.2    Mukhopadhyay, T.3    Helv, T.E.4
  • 58
    • 72849133710 scopus 로고    scopus 로고
    • 21-OH group protected), significantly lower ee's were observed (0% ee and 23% ee)
    • 21-OH group protected), significantly lower ee's were observed (0% ee and 23% ee).
  • 59
    • 72849108453 scopus 로고    scopus 로고
    • 2OH (72% ee), PhOH (70% ee)
    • 2OH (72% ee), PhOH (70% ee).
  • 60
    • 72849142988 scopus 로고    scopus 로고
    • 2 resulted in 11% ee while 20 mol % of 1, ethylene glycol, or ethanolamine gave products with 40-50% ee
    • 2 resulted in 11% ee while 20 mol % of 1, ethylene glycol, or ethanolamine gave products with 40-50% ee.
  • 61
    • 72849106258 scopus 로고    scopus 로고
    • Employment of 1-nitropropane gave results similar to those of nitroethane, but the chiral HPLC separations for these products are not fully resolved using AS-H, AD-H, and OD-H columns. Our full account for these cases will be reported elsewhere
    • Employment of 1-nitropropane gave results similar to those of nitroethane, but the chiral HPLC separations for these products are not fully resolved using AS-H, AD-H, and OD-H columns. Our full account for these cases will be reported elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.