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Volumn , Issue 9, 2009, Pages 1441-1444

Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation

Author keywords

Allylic alkylation; Enantioselectivity; Palladium

Indexed keywords

GAMMA LACTAM DERIVATIVE; PALLADIUM;

EID: 67649365880     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216747     Document Type: Article
Times cited : (22)

References (45)
  • 8
    • 0000585313 scopus 로고    scopus 로고
    • Allylic Substitution Reactions
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin / Heidelberg / New York
    • (b) Pfaltz, A.; Lautens, M. Allylic Substitution Reactions, In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin / Heidelberg / New York, 1999, 834-884.
    • (1999) Comprehensive Asymmetric Catalysis II , pp. 834-884
    • Pfaltz, A.1    Lautens, M.2
  • 18
    • 36049048940 scopus 로고    scopus 로고
    • We assume a reversible pre-equilibrium for the initial complexation between Pd(0)L complex and the double bond of the substrate. (b) Although the enantiodiscriminating step of an AAA is expected to be also the rate-determining one, such a correspondence is not always met in enantioselective transformations. See, for example
    • (a) We assume a reversible pre-equilibrium for the initial complexation between Pd(0)L complex and the double bond of the substrate. (b) Although the enantiodiscriminating step of an AAA is expected to be also the rate-determining one, such a correspondence is not always met in enantioselective transformations. See, for example: Kramer, R.; Brückner, R. Chem. Eur. J. 2007, 13, 9076.
    • (2007) Chem. Eur. J. , vol.13 , pp. 9076
    • Kramer, R.1    Brückner, R.2
  • 21
    • 67649302161 scopus 로고    scopus 로고
    • note
    • 4, and the solvent was removed in vacuo. The crude product was purified by flash chromatography.
  • 23
    • 33645038629 scopus 로고    scopus 로고
    • The er has been preferred to ee as enantioselectivity descriptor. See
    • The er has been preferred to ee as enantioselectivity descriptor. See: Gawley, R. E. J. Org. Chem. 2006, 71, 2411.
    • (2006) J. Org. Chem. , vol.71 , pp. 2411
    • Gawley, R.E.1
  • 24
    • 0033546243 scopus 로고    scopus 로고
    • The absolute configuration of 2 was determined by conversion of an enantioenriched sample of it (er 86:14) into N-benzoyl-3-ethylpyrrolidine and comparison of its optical rotation with that reported for the enantiopure R-configurated sample described by Pedrosa et al.
    • The absolute configuration of 2 was determined by conversion of an enantioenriched sample of it (er 86:14) into N-benzoyl-3-ethylpyrrolidine and comparison of its optical rotation with that reported for the enantiopure R-configurated sample described by Pedrosa et al.: Andres, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273.
    • (1999) J. Org. Chem. , vol.64 , pp. 4273
    • Andres, C.1    Duque-Soladana, J.P.2    Pedrosa, R.3
  • 36
    • 67649323726 scopus 로고    scopus 로고
    • note
    • 4, and the solvent was removed in vacuo. The crude product was purified by flash chromatography.
  • 37
    • 67649356014 scopus 로고    scopus 로고
    • note
    • The instability of this ligand under the basic biphasic conditions might account for this result.
  • 41
    • 27344448074 scopus 로고
    • LACVP* uses the 6-31G* basis set for all light elements, and the Hay-Wadt ECP and basis set for Pd
    • LACVP* uses the 6-31G* basis set for all light elements, and the Hay-Wadt ECP and basis set for Pd: Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
    • (1985) J. Chem. Phys. , vol.82 , pp. 299
    • Hay, P.J.1    Wadt, W.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.