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Volumn 12, Issue , 2008, Pages 302-327

New methods for the asymmetric synthesis of piperidines and pyrrolidines: Chiral auxiliaries and asymmetric organocatalysis

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EID: 79960439464     PISSN: 17249449     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article
Times cited : (13)

References (166)
  • 18
    • 0027960624 scopus 로고
    • For the first use of pseudoephedrine as chiral auxiliary, see: (a)
    • For the first use of pseudoephedrine as chiral auxiliary, see: (a) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9361
    • Myers, A.G.1    Yang, B.H.2    Chen, H.3    Gleason, J.L.4
  • 36
    • 24144459555 scopus 로고    scopus 로고
    • For other selected synthetic approaches to enantioenriched alkylpiperidines from βamino carbonyl derivatives, see: (a)
    • For other selected synthetic approaches to enantioenriched alkylpiperidines from βamino carbonyl derivatives, see: (a) Robertson, J.; Stafford, P. M.; Bell, S. J. J. Org. Chem. 2005, 70, 7133.
    • (2005) J. Org. Chem. , vol.70 , pp. 7133
    • Robertson, J.1    Stafford, P.M.2    Bell, S.J.3
  • 49
    • 33846648075 scopus 로고    scopus 로고
    • For some selected examples on the formation of piperidines via intramolecular reductive amination, see: (a)
    • For some selected examples on the formation of piperidines via intramolecular reductive amination, see: (a) Masuda, Y.; Tashiro, T.; Mori, K. Tetrahedron: Asymmetry 2006, 17, 3380.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3380
    • Masuda, Y.1    Tashiro, T.2    Mori, K.3
  • 59
    • 0042865048 scopus 로고    scopus 로고
    • [α]D 20 = +3.9 (c=1.1, EtOH) for a sample of (R)-pipecoline hydrochloride obtained by us; lit. [α]D 20 =+3.97 (c=1.0, EtOH)
    • [α]D 20 = +3.9 (c=1.1, EtOH) for a sample of (R)-pipecoline hydrochloride obtained by us; lit. [α]D 20 =+3.97 (c=1.0, EtOH). Andres, J. M.; Herraiz-Sierra, I.; Pedrosa, R.; Perez-Encabo A. Eur. J. Org. Chem. 2000, 1719.
    • (2000) Eur. J. Org. Chem. , pp. 1719
    • Andres, J.M.1    Herraiz-Sierra, I.2    Pedrosa, R.3    Perez-Encabo, A.4
  • 60
    • 0000683796 scopus 로고    scopus 로고
    • Compound 8b: [α]D 20 = -1.2 (c=0.2, EtOH); lit. [α]D 20 = -1.42 (c=0.2, EtOH). Ref. 9. Compound 8d:[α]D 20 = +3.0 (c=0.2, EtOH); lit. [α]D 20 = +3.1 (c=0.2, EtOH) for the R isomer
    • Compound 8b: [α]D 20 = -1.2 (c=0.2, EtOH); lit. [α]D 20 = -1.42 (c=0.2, EtOH). Ref. 9. Compound 8d:[α]D 20 = +3.0 (c=0.2, EtOH); lit. [α]D 20 = +3.1 (c=0.2, EtOH) for the R isomer: Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699.
    • (1998) J. Org. Chem. , vol.63 , pp. 6699
    • Katritzky, A.R.1    Qiu, G.2    Yang, B.3    Steel, P.J.4
  • 61
    • 85043573503 scopus 로고    scopus 로고
    • [α]D 20 = +9.0 (c=0.2, EtOH) for a sample of (S)-coniine hydrochloride obtained by us; lit. [α]D 20 = +9.4 (c=0.2, EtOH). Refs. 9 and 10
    • [α]D 20 = +9.0 (c=0.2, EtOH) for a sample of (S)-coniine hydrochloride obtained by us; lit. [α]D 20 = +9.4 (c=0.2, EtOH). Refs. 9 and 10.
  • 93
    • 85043594678 scopus 로고    scopus 로고
    • [α]D 20 = -3.82 (c=0.40, CHCl3) for the (-)-β-conhydrine obtained by us; lit. [α]D 20 = -34.10 (c=0.40, CHCl3). Ref. 15i
    • [α]D 20 = -3.82 (c=0.40, CHCl3) for the (-)-β-conhydrine obtained by us; lit. [α]D 20 = -34.10 (c=0.40, CHCl3). Ref. 15i.
  • 94
    • 79151482263 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim (Germany)
    • Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim (Germany), 2003; Vol. 2, p. 10.
    • (2003) Handbook of Metathesis , vol.2 , pp. 10
    • Grubbs, R.H.1
  • 95
    • 85043572102 scopus 로고    scopus 로고
    • [α]D 20 = -22.20 (c=0.40, CHCl3) for the (-)-β-conhydrine obtained by us; lit. [α]D 20 = -34.10 (c=0.40, CHCl3). Ref. 15i
    • [α]D 20 = -22.20 (c=0.40, CHCl3) for the (-)-β-conhydrine obtained by us; lit. [α]D 20 = -34.10 (c=0.40, CHCl3). Ref. 15i.
  • 96
    • 48849094479 scopus 로고    scopus 로고
    • For selected recent reviews on asymmetric organocatalysis, see: (a)
    • For selected recent reviews on asymmetric organocatalysis, see: (a) Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4638
    • Dondoni, A.1    Massi, A.2
  • 98
    • 85043602888 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • Chem. Rev. 2007, 107 (12), special issue on organocatalysis.
    • (2007) Chem. Rev. , vol.107 , Issue.12
  • 105
    • 85043604687 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • Acc. Chem. Res. 2004, 37 (8), special issue on organocatalysis.
    • (2004) Acc. Chem. Res. , vol.37 , Issue.8
  • 106
    • 23044431676 scopus 로고    scopus 로고
    • For reviews, see: (a)
    • For reviews, see: (a) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
    • (2005) Chem. Rev. , vol.105 , pp. 2765
    • Coldham, I.1    Hufton, R.2
  • 109
    • 33846594443 scopus 로고    scopus 로고
    • For some reviews, see Ref. 1. For some other recent examples not covered by these reviews, see (a)
    • For some reviews, see Ref. 1. For some other recent examples not covered by these reviews, see (a) Zeng, W.; Chen, G.-Y.; Zhou, Y.-G.; Li, Y.-X. J. Am. Chem. Soc. 2007, 129, 750.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 750
    • Zeng, W.1    Chen, G.-Y.2    Zhou, Y.-G.3    Li, Y.-X.4
  • 118
    • 23944490138 scopus 로고    scopus 로고
    • For some recent applications, see (a), and refences therein
    • For some recent applications, see (a) Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 11616, and refences therein.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11616
    • Wilson, R.M.1    Jen, W.S.2    MacMillan, D.W.C.3
  • 119
    • 33744900602 scopus 로고    scopus 로고
    • For other examples, see: (b)
    • For other examples, see: (b) Lemay, M.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 4663.
    • (2006) J. Org. Chem. , vol.71 , pp. 4663
    • Lemay, M.1    Ogilvie, W.W.2
  • 135
    • 0036089366 scopus 로고    scopus 로고
    • For a general review on Michael additions to nitroalkenes, see:
    • For a general review on Michael additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
    • (2002) Eur. J. Org. Chem. , pp. 1877
    • Berner, O.M.1    Tedeschi, L.2    Enders, D.3
  • 161
    • 33845505476 scopus 로고    scopus 로고
    • For an overview on the use of this kind of O-silylated diarylprolinol amines as organocatalysts, see (b)
    • For an overview on the use of this kind of O-silylated diarylprolinol amines as organocatalysts, see (b) Palomo, C.; Mielgo, A. Angew. Chem. Int. Ed. 2006, 45, 7876.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7876
    • Palomo, C.1    Mielgo, A.2
  • 162
    • 22144459070 scopus 로고    scopus 로고
    • For the first examples using this kind of organocatalysts, see (c)
    • For the first examples using this kind of organocatalysts, see (c) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem. Int. Ed. 2005, 44, 4212.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4212
    • Hayashi, Y.1    Gotoh, H.2    Hayashi, T.3    Shoji, M.4
  • 164
    • 79958222806 scopus 로고
    • For a paper highlighting this subject, see Ref. 35h
    • For a paper highlighting this subject, see Ref. 35h Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 1413
    • Seebach, D.1    Golinski, J.2
  • 165
    • 85043578000 scopus 로고    scopus 로고
    • The lower yields of the final pyrrolidines obtained in some cases can be attributed to the fact that single diastereisomers were obtained starting from mixtures of cis/trans precursors which indicated that the minor diastereoisomer was removed during the reaction or the purification of the final product
    • The lower yields of the final pyrrolidines obtained in some cases can be attributed to the fact that single diastereisomers were obtained starting from mixtures of cis/trans precursors which indicated that the minor diastereoisomer was removed during the reaction or the purification of the final product.
  • 166
    • 85043599567 scopus 로고    scopus 로고
    • Reaction of nitroaldehyde 38a with Zn at r.t. furnished pyrrolidine 41a as a 4:1 mixture of diastereoisomers as a result of partial epimerization of C4. This side reaction was avoided by carrying out the reaction at -15 °C and therefore obtaining 41a as a single diastereoisomer
    • Reaction of nitroaldehyde 38a with Zn at r.t. furnished pyrrolidine 41a as a 4:1 mixture of diastereoisomers as a result of partial epimerization of C4. This side reaction was avoided by carrying out the reaction at -15 °C and therefore obtaining 41a as a single diastereoisomer.


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