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Volumn 47, Issue 51, 2008, Pages 9958-9960

Asymmetric synthesis of α-alkylated aldehydes using terminal epoxide-derived chiral enamines

Author keywords

Aldehydes; Alkylation; Asymmetric synthesis; Enamines; Terminal epoxides

Indexed keywords

ALDEHYDES; AMIDES; AMINES; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; HYDROCARBONS; LITHIUM; MATHEMATICAL TRANSFORMATIONS; ORGANIC COMPOUNDS; PORT TERMINALS;

EID: 57549112579     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804369     Document Type: Article
Times cited : (25)

References (34)
  • 5
    • 0002652021 scopus 로고
    • Ed, J. D. Morrison, Academic Press, London
    • a) D. A. Evans in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, London, 1983, pp. 1-110;
    • (1983) Asymmetric Synthesis , vol.3 , pp. 1-110
    • Evans, D.A.1
  • 8
    • 0001269461 scopus 로고
    • for chiral enamine-based asymmetric α-alkylation of cyclohexanone, see
    • b) for chiral enamine-based asymmetric α-alkylation of cyclohexanone, see: J. K. Whitesell, S. W. Fellman, J. Org. Chem. 1977, 42, 1663-1664.
    • (1977) J. Org. Chem , vol.42 , pp. 1663-1664
    • Whitesell, J.K.1    Fellman, S.W.2
  • 10
    • 33646573235 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1952-1956;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1952-1956
  • 11
    • 35048885691 scopus 로고    scopus 로고
    • for a more recent approach to asymmetric ́-allylation, see
    • b) for a more recent approach to asymmetric ́-allylation, see: S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 11336-11337
    • Mukherjee, S.1    List, B.2
  • 13
    • 53349122064 scopus 로고    scopus 로고
    • for recent organocatalytic ́-alkylation using ́-bromocarbonyl compounds, see
    • b) for recent organocatalytic ́-alkylation using ́-bromocarbonyl compounds, see: D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77-80.
    • (2008) Science , vol.322 , pp. 77-80
    • Nicewicz, D.A.1    MacMillan, D.W.C.2
  • 16
    • 57549097649 scopus 로고    scopus 로고
    • Molecular modeling calculations support this analysis: D. M. Hodgson, N. S. Kaka, K. N. Houk, J. M. Um, unpublished results.
    • Molecular modeling calculations support this analysis: D. M. Hodgson, N. S. Kaka, K. N. Houk, J. M. Um, unpublished results.
  • 18
    • 57549086452 scopus 로고
    • J. Org. Chem. USSR 1988, 24, 1836-1840.
    • (1988) J. Org. Chem. USSR , vol.24 , pp. 1836-1840
  • 19
    • 57549115963 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 20
    • 57549086630 scopus 로고    scopus 로고
    • Enamine 5a could be prepared by aldehyde-amine condensation (benzene, Dean-Stark trap, 42 h), but in only 26%yield and as a 4:1 E:Z mixture.
    • Enamine 5a could be prepared by aldehyde-amine condensation (benzene, Dean-Stark trap, 42 h), but in only 26%yield and as a 4:1 E:Z mixture.
  • 23
  • 24
    • 0004087670 scopus 로고
    • Ed, Z. Rappoport, Wiley, Chichester
    • d)The Chemistry of Enamines (Ed.: Z. Rappoport), Wiley, Chichester, 1994;
    • (1994) The Chemistry of Enamines
  • 25
    • 36148949559 scopus 로고    scopus 로고
    • Eds, B. M. Trost, G. A. Molander, Thieme, Stuttgart
    • e) T. Sammakia, J. A. Abramite, M. F. Sammons in Science of Synthesis, Vol. 33 (Eds.: B. M. Trost, G. A. Molander), Thieme, Stuttgart, 2006, pp. 405-441.
    • (2006) Science of Synthesis , vol.33 , pp. 405-441
    • Sammakia, T.1    Abramite, J.A.2    Sammons, M.F.3
  • 26
    • 23944490663 scopus 로고    scopus 로고
    • Attempted C-alkylation using MeI with the enamine derived from MacMillan's imidazolidinone (T. J. Peelen, Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 11598-11599) was not successful.
    • Attempted C-alkylation using MeI with the enamine derived from MacMillan's imidazolidinone (T. J. Peelen, Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 11598-11599) was not successful.
  • 28
    • 34250318651 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 2245-2248;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 2245-2248
  • 33
    • 35748940663 scopus 로고    scopus 로고
    • 1, see: A. Fürstner, M. Bonnekessel, J. T. Blank, K. Radkowski, G. Seidel, F. Lacombe, B. Gabor, R. Mynott, Chem. Eur. J. 2007, 13, 8762-8783.
    • 1, see: A. Fürstner, M. Bonnekessel, J. T. Blank, K. Radkowski, G. Seidel, F. Lacombe, B. Gabor, R. Mynott, Chem. Eur. J. 2007, 13, 8762-8783.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.