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Volumn 131, Issue 41, 2009, Pages 14608-14609

Enantioselective rhodium-catalyzed conjugate alkynylation of 5-benzylidene Meldrum's acids with TMS-acetylene

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATIONS; BENZYLIDENE; BISPHOSPHINE; CHEMICAL EQUATIONS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; GOOD YIELD; MELDRUM'S ACIDS; MILD REACTION; RHODIUM-CATALYZED;

EID: 70350217530     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905336p     Document Type: Article
Times cited : (86)

References (23)
  • 2
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    • Conjugate addition of alkynyl boronates to β-aryl enones catalyzed by 3,3′- diiodobinaphthol: (a)
    • Conjugate addition of alkynyl boronates to β-aryl enones catalyzed by 3,3′- diiodobinaphthol: (a) Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2005, 127, 3244.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3244
    • Wu, T.R.1    Chong, J.M.2
  • 3
    • 0034054973 scopus 로고    scopus 로고
    • Stoichiometric conjugate addition of alkynyl boronates: (b)
    • Stoichiometric conjugate addition of alkynyl boronates: (b) Chong, J. M.; Shen, L.; Taylor, N. J. J. Am. Chem. Soc. 2000, 122, 1822.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1822
    • Chong, J.M.1    Shen, L.2    Taylor, N.J.3
  • 4
    • 4644293034 scopus 로고    scopus 로고
    • Chiral nickel-bisoxazoline complex-catalyzed conjugate addition of dimethylaluminum TMS-acetylide to 2-cyclohexenone: (c)
    • Chiral nickel-bisoxazoline complex-catalyzed conjugate addition of dimethylaluminum TMS-acetylide to 2-cyclohexenone: (c) Kwak, Y.-S.; Corey, E. J. Org. Lett. 2004, 6, 3385.
    • (2004) Org. Lett. , vol.6 , pp. 3385
    • Kwak, Y.-S.1    Corey, E.J.2
  • 5
    • 20544467000 scopus 로고    scopus 로고
    • 2Zn- and chiral amino alcohol-mediated addition of aryl alkynes to nitro olefins under stoichiometric conditions: (d)
    • 2Zn- and chiral amino alcohol-mediated addition of aryl alkynes to nitro olefins under stoichiometric conditions: (d) Yamashita, M.; Yamada, K.; Tomioka, K. Org. Lett. 2005, 7, 2369.
    • (2005) Org. Lett. , vol.7 , pp. 2369
    • Yamashita, M.1    Yamada, K.2    Tomioka, K.3
  • 13
    • 36448967496 scopus 로고    scopus 로고
    • Rh-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols, the synthetic equivalent of asymmetric conjugate alkynylation of enones, has been reported. See
    • Rh-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols, the synthetic equivalent of asymmetric conjugate alkynylation of enones, has been reported. See: Nishimura, T.; Katoh, T.; Takatsu, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14158.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 14158
    • Nishimura, T.1    Katoh, T.2    Takatsu, K.3    Shintani, R.4    Hayashi, T.5
  • 14
    • 67649332168 scopus 로고    scopus 로고
    • Highly electrophilic alkylidene Meldrum's acids have been shown to participate in various conjugate additions under mild reaction conditions. See: (a)
    • Highly electrophilic alkylidene Meldrum's acids have been shown to participate in various conjugate additions under mild reaction conditions. See: (a) Wilsily, A.; Lou, T.; Fillion, E. Synthesis 2009, 2066.
    • (2009) Synthesis , pp. 2066
    • Wilsily, A.1    Lou, T.2    Fillion, E.3
  • 20
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    • note
    • For a complete survey of ligands, see the Supporting Information.
  • 21
    • 70350215436 scopus 로고    scopus 로고
    • note
    • The addition of 4 Å molecular sieves provided consistent yields and ee's.
  • 22
    • 70350233112 scopus 로고    scopus 로고
    • note
    • The absolute stereochemistry of the addition products was determined by comparison with known compound 2r (see ref 3).
  • 23
    • 67649331670 scopus 로고    scopus 로고
    • 3-Substituted phenylpropionic acid is a salient structural motif in medicinal chemistry. See
    • 3-Substituted phenylpropionic acid is a salient structural motif in medicinal chemistry. See: Bharate, S. B.; Nemmani, K. V. S.; Vishwakarma, R. A. Expert Opin. Ther. Pat. 2009, 19, 237.
    • (2009) Expert Opin. Ther. Pat. , vol.19 , pp. 237
    • Bharate, S.B.1    Nemmani, K.V.S.2    Vishwakarma, R.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.