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Volumn 47, Issue 25, 2008, Pages 4687-4690

Organocatalytic asymmetric synthesis of versatile γ-lactams

Author keywords

Asymmetric catalysis; Cinchona alkaloids; Natural products; Phase transfer catalysis; Vinylic substitution

Indexed keywords

AMIDES;

EID: 48849091242     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800329     Document Type: Article
Times cited : (44)

References (51)
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  • 7
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    • for synthesis of salinosporamide A, see: b L. R. Reddy, P. Saravanen, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 6230;
    • for synthesis of salinosporamide A, see: b) L. R. Reddy, P. Saravanen, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 6230;
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    • reviews: for synthesis of dysibetaine, see: f
    • for synthesis of dysibetaine, see: f) B. B. Snider, Y. Gu, Org. Lett. 2001, 3, 1761; reviews:
    • (2001) Org. Lett , vol.3 , pp. 1761
    • Snider, B.B.1    Gu, Y.2
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    • Reviews on organocatalysis: a
    • Reviews on organocatalysis: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
    • (2001) Angew. Chem , vol.113 , pp. 3840
    • Dalko, P.I.1    Moisan, L.2
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    • issue on organocatalysis;
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    • Ed, P. I. Dalko, Wiley-VCH, Weinheim
    • e) Enantioselective Organocatalysis (Ed.: P. I. Dalko), Wiley-VCH, Weinheim, 2007.
    • (2007) Enantioselective Organocatalysis
  • 36
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    • for recent reviews of asymmetric phase-transfer catalysis, see: b, 2nd ed, Ed, I. Ojima, Wiley-VCH, Weinheim
    • for recent reviews of asymmetric phase-transfer catalysis, see: b) M. J. O'Donnell in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, pp. 727-755;
    • (2000) Catalytic Asymmetric Synthesis , pp. 727-755
    • O'Donnell in, M.J.1
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    • For previous examples of 1,2-dinucleophiles used to construct pyrrolidin-2-ones with Michael reactions, see: a L. Marzorati, M. C. de Mattos, B. Wladislaw, C. de Vita, Synth. Commun. 2002, 32, 1427;
    • For previous examples of 1,2-dinucleophiles used to construct pyrrolidin-2-ones with Michael reactions, see: a) L. Marzorati, M. C. de Mattos, B. Wladislaw, C. de Vita, Synth. Commun. 2002, 32, 1427;
  • 47
    • 53349115527 scopus 로고    scopus 로고
    • This strategy has been employed previously to reduce the enantioselectivity differences between quasi-enantiomeric cinchona alkaloid catalysts involved in Pt-cinchona catalyzed enantioselective hydrogenation, see: H.-U. Blaser, S. Burkhardt, H. J. Kirner, T. Mössner, M. Studer, Synthesis 2003, 1679. We have found that if isoCd-1 is pretreated with MeOH and silica gel (see the Supporting Information, the enantioselectivity of crude ent-4b can be increased to 94% ee. At present we do not know the reason for this effect and have therefore decided not to report this ee value in Table 1. However, this method was used to prepare ent-4b on a gram scale. The reaction was performed using 1.5 mol% catalyst: ent-4b: 94% ee crude, 78% yield, >99% ee
    • This strategy has been employed previously to reduce the enantioselectivity differences between quasi-enantiomeric cinchona alkaloid catalysts involved in Pt-cinchona catalyzed enantioselective hydrogenation, see: H.-U. Blaser, S. Burkhardt, H. J. Kirner, T. Mössner, M. Studer, Synthesis 2003, 1679. We have found that if isoCd-1 is pretreated with MeOH and silica gel (see the Supporting Information), the enantioselectivity of crude ent-4b can be increased to 94% ee. At present we do not know the reason for this effect and have therefore decided not to report this ee value in Table 1. However, this method was used to prepare ent-4b on a gram scale. The reaction was performed using 1.5 mol% catalyst: ent-4b: 94% ee (crude), 78% yield, >99% ee.
  • 48
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    • CCDC 675042 (4a), 675043 (4b), 675044 (10), and 675045 (11), contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • CCDC 675042 (4a), 675043 (4b), 675044 (10), and 675045 (11), contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


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