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Volumn 7, Issue 19, 2005, Pages 4253-4256

Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones

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EID: 25444470782     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0517729     Document Type: Article
Times cited : (244)

References (49)
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, Chapter 31.2
    • (c) Yamaguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999; Chapter 31.2.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Yamaguchi, M.1
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    • For recent reviews, see: (a) Miller, S. J. Acc. Chem. Res. 2004, 37,601-610.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 601-610
    • Miller, S.J.1
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    • 23944490663 scopus 로고    scopus 로고
    • ASAP (DOI: 10.1021/ja0532584)
    • Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, ASAP (DOI: 10.1021/ja0532584). In this study, an enamine intermediate was observed. High catalyst loading (20 mol %) was required, and the ee values were 82-92%.
    • (2005) J. Am. Chem. Soc.
    • Peelen, T.J.1    Chi, Y.2    Gellman, S.H.3
  • 29
    • 23944480330 scopus 로고    scopus 로고
    • Enantiomeric excess in initial studies was determined by an NMR assay; see: Chi, Y.; Peelen, T. J.; Gellman. S. H. Org. Lett. 2005, 7, 3469-3472.
    • (2005) Org. Lett. , vol.7 , pp. 3469-3472
    • Chi, Y.1    Peelen, T.J.2    Gellman, S.H.3
  • 30
    • 0037279171 scopus 로고    scopus 로고
    • C forms cyclic aminals with both aromatic and aliphatic aldehydes under anhydrous acidic conditions. For examples, see: Zuo, G.; Zhang, Q.; Xu, J. Heteroatom Chem. 2003, 14, 42-45.
    • (2003) Heteroatom Chem. , vol.14 , pp. 42-45
    • Zuo, G.1    Zhang, Q.2    Xu, J.3
  • 32
    • 0037157154 scopus 로고    scopus 로고
    • For an example of α-substituted aldehyde product racemization by catalyst, see: List, B. J. Am. Chem. Soc. 2002, 124, 5656-5657.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5656-5657
    • List, B.1
  • 33
    • 25444473091 scopus 로고    scopus 로고
    • note
    • (a) Without catechol cocatalyst, these reactions gave only 1-35% conversion after 48 h, except for reaction of hydrocinnamaldehyde and ethyl vinyl ketone (63% conversion).
  • 34
    • 25444520449 scopus 로고    scopus 로고
    • note
    • (b) The use of catechol cocatalyst enhances the reaction rates in all cases.
  • 35
    • 0346865819 scopus 로고    scopus 로고
    • For reviews of hydrogen bonding in catalysis, see: Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296.
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 289-296
    • Schreiner, P.R.1
  • 41
    • 25444435337 scopus 로고    scopus 로고
    • note
    • Other mechanisms of activation such as catechol catalysis of initial enamine formation cannot be ruled out at this time.
  • 45
    • 25444454008 scopus 로고    scopus 로고
    • note
    • Ref 16 reported a single Michael addition, hydrocinnamaldehyde to methyl vinyl ketone, with 30 mol % H, giving 52% yield and 97% ee; reaction time and temperature were not given.


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