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Volumn 48, Issue 43, 2009, Pages 8060-8062

Cationic-oxazaborolidine-catalyzed enantioselective diels-alder reaction of a,b-unsaturated acetylenic ketones

Author keywords

Acetylenes; Asymmetric catalysis; Boron; Diels alder reaction; Oxazaborolidines

Indexed keywords

ACETYLENIC KETONES; ACYCLIC DIENES; ASYMMETRIC CATALYSIS; ASYMMETRIC INDUCTION; DIELS ALDER ADDUCTS; DIELS ALDER REACTION; DIENOPHILES; ENANTIOSELECTIVE DIELS-ALDER REACTIONS; HYDROGEN BONDING MOTIFS; OXAZABOROLIDINE; OXAZABOROLIDINES; TRIMETHYLSILYL;

EID: 70349974590     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904339     Document Type: Article
Times cited : (48)

References (29)
  • 1
    • 0002448280 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • D. A. Evans, J. S. Johnson in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 33.1.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 33
    • Evans, D.A.1    Johnson, J.S.2
  • 3
    • 0036259981 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 1668-1698.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1668-1698
  • 5
  • 6
    • 61949362917 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 2100-2117;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2100-2117
  • 8
    • 16244422698 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1484-1487;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1484-1487
  • 10
    • 45249121299 scopus 로고    scopus 로고
    • (Eds.: H. Yamamoto, K. Ishihara), Wiley-VCH, Weinheim
    • e) Acid Catalysis in Modern Organic Synthesis, Vol. 1 (Eds.: H. Yamamoto, K. Ishihara), Wiley-VCH, Weinheim, 2008.
    • (2008) Acid Catalysis in Modern Organic Synthesis , vol.1
  • 17
    • 34547752028 scopus 로고    scopus 로고
    • In contrast, the catalyst EtAlCl2 (20 mol %) gives the adducts of ethyl acrylate and 1- and 2-methylcyclopentadiene in a 7:3 ratio; it thus favors the formation of the product derived from 2-methylcyclopentadiene.
    • J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9536-9537. In contrast, the catalyst EtAlCl2 (20 mol %) gives the adducts of ethyl acrylate and 1- and 2-methylcyclopentadiene in a 7:3 ratio; it thus favors the formation of the product derived from 2-methylcyclopentadiene.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9536-9537
    • Payette, J.N.1    Yamamoto, H.2
  • 18
    • 2742569677 scopus 로고
    • For a discussion of the ?-silicon effect, see
    • For a discussion of the ?-silicon effect, see: J. B. Lambert, Tetrahedron 1990, 46, 2677-2689.
    • (1990) Tetrahedron , vol.46 , pp. 2677-2689
    • Lambert, J.B.1
  • 21
    • 17644414916 scopus 로고    scopus 로고
    • For oxazaborolidinium activation of methyl aryl ketones, see:
    • For oxazaborolidinium activation of methyl aryl ketones, see: a) D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 5384-5387;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5384-5387
    • Ryu, D.H.1    Corey, E.J.2
  • 22
    • 0035822774 scopus 로고    scopus 로고
    • For a discussion of the role of hydrogen bonding in enantioselective Lewis acid catalysis, see
    • For a discussion of the role of hydrogen bonding in enantioselective Lewis acid catalysis, see : b) E. J. Corey, T. W Lee, Chem. Commun. 2001, 1321-1329.
    • (2001) Chem. Commun. , pp. 1321-1329
    • Corey, E.J.1    W Lee, T.2
  • 23
    • 58149176972 scopus 로고    scopus 로고
    • DFT studies on oxazaborolidinium catalysis suggest that hydrogen bonding between the catalyst and the substrate may not always occur
    • a) DFT studies on oxazaborolidinium catalysis suggest that hydrogen bonding between the catalyst and the substrate may not always occur: M. N. Paddon-Row, L. C. H. Kwan, A. C. Willis, M. S. Sherburn, Angew. Chem. 2008, 120, 7121-7125;
    • (2008) Angew. Chem. , vol.120 , pp. 7121-7125
    • Paddon-Row, M.N.1    Kwan, L.C.H.2    Willis, A.C.3    Sherburn, M.S.4
  • 24
    • 84962384555 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7013-7017;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7013-7017
  • 25
    • 34648829990 scopus 로고    scopus 로고
    • For experimental support for these findings, see
    • For experimental support for these findings, see: b) E. P. Balskus, E. N. Jacobsen, Science 2007, 317, 1736-1740.
    • (2007) Science , vol.317 , pp. 1736-1740
    • Balskus, E.P.1    Jacobsen, E.N.2
  • 26
    • 0001015795 scopus 로고    scopus 로고
    • For a discussion of the Corey-Bakshi-Shibata (CBS) reduction of alkynyl ketones, see
    • For a discussion of the Corey-Bakshi-Shibata (CBS) reduction of alkynyl ketones, see : E. J. Corey, C J. Helal, Angew. Chem. 1998, 110, 2092-2118;
    • (1998) Angew. Chem. , vol.110 , pp. 2092-2118
    • Corey, E.J.1    Helal C, J.2
  • 27
    • 0032541271 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1986-2012
  • 28
    • 70349954897 scopus 로고    scopus 로고
    • The X-ray crystal structure does not indicate the presence of a hydrogen bond between O2-H and O3.
    • The X-ray crystal structure does not indicate the presence of a hydrogen bond between O2-H and O3.
  • 29
    • 70349964539 scopus 로고    scopus 로고
    • Acetylenic esters were screened as dienophiles with various cyclic and acyclic dienes. However, presumably as a result of their lower reactivity, no product was detected.
    • Acetylenic esters were screened as dienophiles with various cyclic and acyclic dienes. However, presumably as a result of their lower reactivity, no product was detected.


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