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Volumn 132, Issue 34, 2010, Pages 11884-11886

Chiral brønsted acid-catalyzed allylboration of aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; ALLYLBORATION; BORONATE; ENANTIOSELECTIVE; ENANTIOSELECTIVE ALLYLATION; HIGH REACTIVITY; NEW HIGH; REACTION CONDITIONS; STANDING PROBLEMS;

EID: 77956083804     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja104956s     Document Type: Article
Times cited : (219)

References (57)
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    • Otera J., Ed.; Wiley-VCH: Weinheim, Germany,; Chapter 10
    • Denmark, S. E. and Almstead, N. G. In Modern Carbonyl Chemisry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 10, p 299.
    • (2000) Modern Carbonyl Chemisry , pp. 299
    • Denmark, S.E.1    Almstead, N.G.2
  • 6
    • 0002446724 scopus 로고
    • Trost B.M., Ed.; Pergamon Press: Oxford, U.K
    • Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 13
    • 0000995725 scopus 로고
    • For selected examples of chirally modified allyl reagents, see
    • For selected examples of chirally modified allyl reagents, see: Roush, W. R., Walts, A. E., and Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 8186
    • Roush, W.R.1    Walts, A.E.2    Hoong, L.K.3
  • 44
    • 38349189109 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see: Akiyama, T. Chem. Rev. 2007, 107, 5744
    • (2007) Chem. Rev. , vol.107 , pp. 5744
    • Akiyama, T.1
  • 50
    • 0242432417 scopus 로고    scopus 로고
    • For selected Brønsted acid activation of carbonyl compounds other than phosphoric acids, see
    • For selected Brønsted acid activation of carbonyl compounds other than phosphoric acids, see: Huang, Y., Unni, A. K., Thadani, A. N., and Rawal, V. H. Nature 2003, 424, 146
    • (2003) Nature , vol.424 , pp. 146
    • Huang, Y.1    Unni, A.K.2    Thadani, A.N.3    Rawal, V.H.4
  • 54
    • 28044438742 scopus 로고    scopus 로고
    • See the Supporting Information for details on catalyst screening. Both enantiomers of TRIP-PA (R and S) are commercially available or easily prepared from BINOL using a literature procedure (see:)
    • See the Supporting Information for details on catalyst screening. Both enantiomers of TRIP-PA (R and S) are commercially available or easily prepared from BINOL using a literature procedure (see: Hoffmann, S., Seayad, A., and List, B. Angew. Chem., Int. Ed. 2005, 44, 7424)
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7424
    • Hoffmann, S.1    Seayad, A.2    List, B.3
  • 55
    • 77956075654 scopus 로고    scopus 로고
    • The most notable comparison is the work by Hall (ref 5c-5g), which used a chiral diol/tin(IV) chloride combination to generate a Lewis acid/Brønsted acid-catalyzed allylboration
    • The most notable comparison is the work by Hall (ref 5c-5g), which used a chiral diol/tin(IV) chloride combination to generate a Lewis acid/Brønsted acid-catalyzed allylboration.


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