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Volumn 130, Issue 9, 2008, Pages 2746-2747

Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: Design of effective monodentate TADDOL-like phosphonite ligands

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PHOSPHONITE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG; VINYL KETONE DERIVATIVE;

EID: 40949114623     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710862u     Document Type: Article
Times cited : (87)

References (52)
  • 1
    • 34347225080 scopus 로고    scopus 로고
    • For an excellent review of the reductive aldol reaction, see
    • For an excellent review of the reductive aldol reaction, see: Nishiyama, H.; Shiomi, T. Top. Curr. Chem. 2007, 279, 105.
    • (2007) Top. Curr. Chem , vol.279 , pp. 105
    • Nishiyama, H.1    Shiomi, T.2
  • 2
    • 0000191874 scopus 로고
    • For rhodium catalyzed reductive aldol reaction mediated by silane, see: a
    • For rhodium catalyzed reductive aldol reaction mediated by silane, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
    • (1987) Tetrahedron Lett , vol.28 , pp. 4809
    • Revis, A.1    Hilty, T.K.2
  • 15
    • 0037176242 scopus 로고    scopus 로고
    • For rhodium catalyzed reductive aldol reaction mediated by hydrogen, see: a
    • For rhodium catalyzed reductive aldol reaction mediated by hydrogen, see: (a) Jang, H. Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 15156
    • Jang, H.Y.1    Huddleston, R.R.2    Krische, M.J.3
  • 21
    • 33845917794 scopus 로고    scopus 로고
    • Jung, C. K.; Krische, M, J. J. Am. Chem. Soc. 2006, 128, 17051.
    • (g) Jung, C. K.; Krische, M, J. J. Am. Chem. Soc. 2006, 128, 17051.
  • 22
    • 40949163009 scopus 로고    scopus 로고
    • For catalytic reductive aldol couplings using other metals, see: (a) (Cobalt) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005.
    • For catalytic reductive aldol couplings using other metals, see: (a) (Cobalt) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005.
  • 38
    • 33847032528 scopus 로고    scopus 로고
    • Nickel: Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537. (Indium)
    • (q) Nickel: Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537. (Indium)
  • 43
    • 21244479264 scopus 로고    scopus 로고
    • Other organocatalysts for direct aldol coupling of 2-butanone generally provide mixtures of regioisomers: Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285.
    • (c) Other organocatalysts for direct aldol coupling of 2-butanone generally provide mixtures of regioisomers: Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285.
  • 45
    • 0000131734 scopus 로고    scopus 로고
    • 3P effects in metal catalysis, see: (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
    • 3P effects in metal catalysis, see: (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
  • 51
    • 40949111615 scopus 로고    scopus 로고
    • Aromatic aldehydes display good reactivity and diastereoselectivity, but poor enantioselectivities are observed. Additionally, unactivated aliphatic aldehydes exhibit poor reactivity, providing diminished yields of product. Studies aimed at addressing these deficiencies are in progress
    • Aromatic aldehydes display good reactivity and diastereoselectivity, but poor enantioselectivities are observed. Additionally, unactivated aliphatic aldehydes exhibit poor reactivity, providing diminished yields of product. Studies aimed at addressing these deficiencies are in progress.
  • 52
    • 40949103684 scopus 로고    scopus 로고
    • The absolute stereochemical assignments of the aldol adducts are made in analogy to that determined for the 5-bromophthalimido derivative of aldol adduct 1b and the 2-bromo-5-nitrobenzoate of 3b, which were established by single crystal X-ray diffraction analysis using the anomalous dispersion method
    • The absolute stereochemical assignments of the aldol adducts are made in analogy to that determined for the 5-bromophthalimido derivative of aldol adduct 1b and the 2-bromo-5-nitrobenzoate of 3b, which were established by single crystal X-ray diffraction analysis using the anomalous dispersion method.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.