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Volumn 11, Issue 15, 2009, Pages 3270-3273

Highly regio- and enantioselective organocatalytic conjugate addition of alkyl methyl ketones TO A β-silylmethylene malonate

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ANISOMYCIN; BETA SILYLMETHYLENE MALONATE; BETA-SILYLMETHYLENE MALONATE; DRUG DERIVATIVE; KETONE; MALONIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PREUSSIN; PYRROLIDINE DERIVATIVE;

EID: 68149147424     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900803n     Document Type: Article
Times cited : (37)

References (72)
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    • (2002) Science of Synthesis , vol.4 , pp. 927
    • Fleming, I.1
  • 2
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    • For a review on silicon-controlled stereoselective reactions, see
    • For a review on silicon-controlled stereoselective reactions, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
    • (1997) Chem. Rev , vol.97 , pp. 2063
    • Fleming, I.1    Barbero, A.2    Walter, D.3
  • 11
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    • and references cited therein. For recent methodologies, see
    • For recent methodologies, see: Walter, C.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 3818, and references cited therein.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 3818
    • Walter, C.1    Oestreich, M.2
  • 13
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    • Selected reviews:(a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
    • Selected reviews:(a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
  • 27
    • 0000761777 scopus 로고    scopus 로고
    • Selected examples:(a) List, B.; Pojarlier, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
    • Selected examples:(a) List, B.; Pojarlier, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
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    • Cao, C.-L.; Sun, X. -Li; Zhou, J.,- L.; Tang, Y. J. Org. Chem. 2007, 72, 4073.
    • Cao, C.-L.; Sun, X. -Li; Zhou, J.,- L.; Tang, Y. J. Org. Chem. 2007, 72, 4073.
  • 49
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    • Selected examples:(a) Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570.
  • 58
    • 0348248914 scopus 로고    scopus 로고
    • For asymmetric Michael addition of preformed enamines derived from chiral amines to nitroalkenes and alkylidene malonates, see:(a) Blarer, S. J, Seebach, D. Chem. Ber. 1983, 116, 2250
    • For asymmetric Michael addition of preformed enamines derived from chiral amines to nitroalkenes and alkylidene malonates, see:(a) Blarer, S. J.; Seebach, D. Chem. Ber. 1983, 116, 2250.
  • 70
    • 68149086853 scopus 로고    scopus 로고
    • Reaction of diethyl 4-fluorobenzylidene malonate with methyl ethyl ketone in the presence of catalyst 6c and TFA in NMP at 28 °C gave a ∼3:. See the Supporting Information for details
    • Reaction of diethyl 4-fluorobenzylidene malonate with methyl ethyl ketone in the presence of catalyst 6c and TFA in NMP at 28 °C gave a ∼3:2 mixture of regioisomers with Me end addition product as the major. See the Supporting Information for details.
    • 2 mixture of regioisomers with Me end addition product as the major
  • 71
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    • Enantiomeric excess of 8 was found to be 90% by HPLC analysis.
    • Enantiomeric excess of 8 was found to be 90% by HPLC analysis.
  • 72
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    • Hydrolysis of β-silyl esters do not epimerize the β-C center. See ref 3
    • Hydrolysis of β-silyl esters do not epimerize the β-C center. See ref 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.