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Volumn 130, Issue 31, 2008, Pages 10076-10077

Enantio- and diastereoselective catalytic alkylation reactions with aziridines

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; AZIRIDINE DERIVATIVE;

EID: 48749115535     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8036965     Document Type: Article
Times cited : (97)

References (34)
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    • For recent reviews, see: a
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    • (2007) Tetrahedron , vol.63 , pp. 9267
    • Pellissier, H.1
  • 5
    • 42649142295 scopus 로고    scopus 로고
    • For recent examples of secondary amine catalyzed Michael additions of aldehydes to nitroolefins, see: a
    • For recent examples of secondary amine catalyzed Michael additions of aldehydes to nitroolefins, see: (a) Chi, Y.; Guo, L.; Kopf, N. A.; Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 5608.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 5608
    • Chi, Y.1    Guo, L.2    Kopf, N.A.3    Gellman, S.H.4
  • 9
    • 85044709894 scopus 로고
    • For early studies using β-haloamines as electrophiles in β-ketoester alkylations, see
    • For early studies using β-haloamines as electrophiles in β-ketoester alkylations, see: Barltrop, J. A. J. Chem. Soc. 1947, 399.
    • (1947) J. Chem. Soc , pp. 399
    • Barltrop, J.A.1
  • 10
    • 33751333267 scopus 로고    scopus 로고
    • For reviews on ring opening of aziridines, including asymmetric methods, see: a
    • For reviews on ring opening of aziridines, including asymmetric methods, see: (a) Pineschi, M. Eur. J. Org. Chem. 2006, 4979.
    • (2006) Eur. J. Org. Chem , pp. 4979
    • Pineschi, M.1
  • 12
  • 13
    • 44049101018 scopus 로고    scopus 로고
    • and references cited therein. For a base-catalyzed process, see
    • For a base-catalyzed process, see: Moss, T. A.; Alba, A.; Hepworth, D.; Dixon, D. J. Chem Commun. 2008, 21, 2474 and references cited therein.
    • (2008) Chem Commun , vol.21 , pp. 2474
    • Moss, T.A.1    Alba, A.2    Hepworth, D.3    Dixon, D.J.4
  • 18
    • 33845185214 scopus 로고
    • For selected examples of advances in asymmetric phase transfer catalysis, see: a
    • For selected examples of advances in asymmetric phase transfer catalysis, see: (a) O'Donnell, M. J.; Bennet, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 2353
    • O'Donnell, M.J.1    Bennet, W.D.2    Wu, S.3
  • 31
    • 48749117541 scopus 로고    scopus 로고
    • 3(s) was found to be optimal.
    • 3(s) was found to be optimal.
  • 32
    • 0003463148 scopus 로고    scopus 로고
    • For deprotection procedures, see:, Wuts, P. G. M, Greene, T. W, Eds, Wiley: New York
    • For deprotection procedures, see: Protective Groups in Organic Synthesis; Wuts, P. G. M., Greene, T. W., Eds.; Wiley: New York, 2007.
    • (2007) Protective Groups in Organic Synthesis
  • 33
    • 48749120149 scopus 로고    scopus 로고
    • Using 4f and Cs2CO3s, good reactivity but poor diastereomeric ratios were observed with a range of noncyclic phenyl cyanoacetate nucleophiles
    • 3(s), good reactivity but poor diastereomeric ratios were observed with a range of noncyclic phenyl cyanoacetate nucleophiles.


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