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Volumn 11, Issue 3, 2009, Pages 677-680

Stereodivergency of triazolium and imidazolium-derived NHcs for catalytic, enantioselective cyclopentane synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; IMIDAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE;

EID: 60849120146     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802739d     Document Type: Article
Times cited : (119)

References (26)
  • 8
    • 7744232978 scopus 로고    scopus 로고
    • For the first reports, see: a
    • For the first reports, see: (a) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 14370-14371
    • Sohn, S.S.1    Rosen, E.L.2    Bode, J.W.3
  • 17
    • 0027175468 scopus 로고
    • For reviews on β-lactone chemistry, see: a
    • For reviews on β-lactone chemistry, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-459.
    • (1993) Synthesis , pp. 441-459
    • Pommier, A.1    Pons, J.-M.2
  • 19
    • 33749027460 scopus 로고    scopus 로고
    • Romo has reported that [3.2.0]bicyclic β-lactone bearing aliphatic substituents do not undergo spontaneous decarboxylation: Henry-Riyad, H.; Lee, C; Purohit, V. C.; Romo, D. Org. Lett. 2006, 8, 4363-4366.
    • (c) Romo has reported that [3.2.0]bicyclic β-lactone bearing aliphatic substituents do not undergo spontaneous decarboxylation: Henry-Riyad, H.; Lee, C; Purohit, V. C.; Romo, D. Org. Lett. 2006, 8, 4363-4366.
  • 20
    • 34548159194 scopus 로고    scopus 로고
    • This limitation can be overcome if the reaction is run in an intramolecular fashion: Wadamoto, M, Phillips, E. M, Reynolds, T. E, Scheldt, K. A J. Am. Chem. Soc. 2007, 129, 10098-10099
    • This limitation can be overcome if the reaction is run in an intramolecular fashion: Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheldt, K. A J. Am. Chem. Soc. 2007, 129, 10098-10099.
  • 21
    • 0242582901 scopus 로고    scopus 로고
    • For the use of achiral α-hydroxy enones in asymmetric catalysis, see: a
    • For the use of achiral α-hydroxy enones in asymmetric catalysis, see: (a) Palomo, C.; Oiarbide, M.; García, J. M.; González, A.; Arceo, E. J. Am. Chem. Soc. 2003, 125, 13942-13943.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 13942-13943
    • Palomo, C.1    Oiarbide, M.2    García, J.M.3    González, A.4    Arceo, E.5
  • 23
    • 40149107472 scopus 로고    scopus 로고
    • We have reported the synthesis of β-lactams from chalcone-derived imines: He, M, Bode, J. J. Am. Chem. Soc. 2008, 130, 418-419. Imidazolium 2-C1O4 is ineffective for these reactions
    • 4 is ineffective for these reactions.
  • 24
    • 62149094437 scopus 로고    scopus 로고
    • 4 was used for some entries (see the Supporting Information). Identical results were obtained with 2 for the preparation of the other enantiomers. No effect of the counterion was detected, and the change in counterion between the catalysts types does not affect the stereochemical outcome.
    • 4 was used for some entries (see the Supporting Information). Identical results were obtained with 2 for the preparation of the other enantiomers. No effect of the counterion was detected, and the change in counterion between the catalysts types does not affect the stereochemical outcome.
  • 25
    • 43549123600 scopus 로고    scopus 로고
    • 4, see: (a) Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Org. Lett. 2008, 10, 957-960.
    • 4, see: (a) Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Org. Lett. 2008, 10, 957-960.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.