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Volumn 129, Issue 8, 2007, Pages 2248-2249

Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKADIENE; BISHOMOALLYLIC ALCOHOL DERIVATIVE; NICKEL COMPLEX; PHOSPHORAMIDOUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847652798     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0693183     Document Type: Article
Times cited : (118)

References (32)
  • 1
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    • For reviews, see: a
    • For reviews, see: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
    • (2001) Chem. Rev , vol.101 , pp. 757
    • Pu, L.1    Yu, H.-B.2
  • 5
    • 84891322500 scopus 로고    scopus 로고
    • For reviews on the Ni-catalyzed dienes-carbonyl reductive coupling, see: a, Tamaru, Y, Ed, Wiley-VCH: Weinheim, Germany
    • For reviews on the Ni-catalyzed dienes-carbonyl reductive coupling, see: (a) Modern Organo Nickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Modern Organo Nickel Chemistry
  • 9
    • 0001142313 scopus 로고    scopus 로고
    • For dienes-carbonyl reductive couplings catalyzed by other transition metals, see: e
    • For dienes-carbonyl reductive couplings catalyzed by other transition metals, see: (e) Takai, K.; Toratsu, C. J. Org. Chem. 1998, 63, 6450.
    • (1998) J. Org. Chem , vol.63 , pp. 6450
    • Takai, K.1    Toratsu, C.2
  • 20
    • 0037467387 scopus 로고    scopus 로고
    • For Ni-catalyzed asymmetric reductive coupling of alkynes and enynes, see: a
    • For Ni-catalyzed asymmetric reductive coupling of alkynes and enynes, see: (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 3442
    • Miller, K.M.1    Huang, W.-S.2    Jamison, T.F.3
  • 23
    • 33845961272 scopus 로고    scopus 로고
    • For Rh-catalyzed asymmetric reductive coupling of enynes, see: d
    • For Rh-catalyzed asymmetric reductive coupling of enynes, see: (d) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16448
    • Komanduri, V.1    Krische, M.J.2
  • 30
    • 33744795735 scopus 로고    scopus 로고
    • For the mechanism of Ni-catalyzed reductive coupling of dienes and carbonyl compounds, see: Ogoshi, S.; Tonomori, K.-J.; Oka, M.-A.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 7077. See also ref 5.
    • For the mechanism of Ni-catalyzed reductive coupling of dienes and carbonyl compounds, see: Ogoshi, S.; Tonomori, K.-J.; Oka, M.-A.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 7077. See also ref 5.
  • 31
    • 33847637852 scopus 로고    scopus 로고
    • For the details of preparation and analysis of new ligands, see Supporting Information
    • For the details of preparation and analysis of new ligands, see Supporting Information.
  • 32
    • 33847687520 scopus 로고    scopus 로고
    • The coupling of aliphatic dienes such as 1,3-butadiene and 2-methyl-1,3-butadiene with benzaldehyde gave a mixture of bishomoallylic alcohol and homoallylic alcohol with low regioselectivity and enantioselectivity
    • The coupling of aliphatic dienes such as 1,3-butadiene and 2-methyl-1,3-butadiene with benzaldehyde gave a mixture of bishomoallylic alcohol and homoallylic alcohol with low regioselectivity and enantioselectivity.


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