메뉴 건너뛰기




Volumn 130, Issue 45, 2008, Pages 14984-14986

Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZIRIDINE DERIVATIVE; EPISULFONIUM ION; MESOAZIRIDINIUM; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57349134538     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806431d     Document Type: Article
Times cited : (180)

References (42)
  • 1
    • 1542475798 scopus 로고    scopus 로고
    • For a review on chiral anions, see
    • For a review on chiral anions, see: Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373.
    • (2003) Chem. Soc. Rev , vol.32 , pp. 373
    • Lacour, J.1    Hebbe-Viton, V.2
  • 4
    • 0842279656 scopus 로고    scopus 로고
    • Another study: (c) Dorta, R.; Shimon, L.; Milstein, D. J. Organomet. Chem. 2004, 689, 751.
    • Another study: (c) Dorta, R.; Shimon, L.; Milstein, D. J. Organomet. Chem. 2004, 689, 751.
  • 7
    • 33845961272 scopus 로고    scopus 로고
    • For examples of chiral Brønsted acids used in cooperation with transition metals, see:(a) Komanduri, V, Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448
    • For examples of chiral Brønsted acids used in cooperation with transition metals, see:(a) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
  • 13
    • 30744477746 scopus 로고    scopus 로고
    • For a related study using Brønsted acid catalysis, see:(e) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
    • For a related study using Brønsted acid catalysis, see:(e) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
  • 16
    • 57349162719 scopus 로고    scopus 로고
    • As early as ref 6b the limiting case transition state of fully ionized phosphate/iminium ion pair was proposed, thereby foreshadowing the future developments in chiral counteranion chemistry
    • As early as ref 6b the limiting case transition state of fully ionized phosphate/iminium ion pair was proposed, thereby foreshadowing the future developments in chiral counteranion chemistry.
  • 17
    • 38349189109 scopus 로고    scopus 로고
    • Reviews on chiral Brønsted acids: (a) Akiyama, T
    • Reviews on chiral Brønsted acids: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
    • (2007) Chem. Rev , vol.107 , pp. 5744
  • 23
    • 38849199300 scopus 로고    scopus 로고
    • For use of a stoichiometric chiral anion in an asymmetric Stevens rearrangement: Gonçalves-Farbos, M-H.; Vial, L.; Lacour, J. Chem. Commun. 2008, 829.
    • For use of a stoichiometric chiral anion in an asymmetric Stevens rearrangement: Gonçalves-Farbos, M-H.; Vial, L.; Lacour, J. Chem. Commun. 2008, 829.
  • 24
    • 34447272888 scopus 로고    scopus 로고
    • Reviews on chiral phase transfer catalysis: a
    • Reviews on chiral phase transfer catalysis: (a) Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 4222
    • Ooi, T.1    Maruoka, K.2
  • 25
    • 0001851179 scopus 로고    scopus 로고
    • 2nd ed, Ojima, I, Ed, Wiley-VCH: New York, Chapter 10, pp
    • (b) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10, pp 727-755.
    • (2000) Catalytic Asymmetric Synthesis , pp. 727-755
    • O'Donnell, M.J.1
  • 28
    • 41849101500 scopus 로고    scopus 로고
    • For selected recent examples of chiral cation phase transfer catalysis, see: a
    • For selected recent examples of chiral cation phase transfer catalysis, see: (a) Elsner, P.; Bemardi, L.; Salla, G. D.; Overgaard, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2008, 130, 4897.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 4897
    • Elsner, P.1    Bemardi, L.2    Salla, G.D.3    Overgaard, J.4    Jørgensen, K.A.5
  • 32
    • 57349127198 scopus 로고    scopus 로고
    • Many chiral phase transfer reactions go by an interfacial mechanism; this is possible for our concept also but is not shown for simplicity
    • Many chiral phase transfer reactions go by an interfacial mechanism; this is possible for our concept also but is not shown for simplicity.
  • 34
    • 34250870785 scopus 로고    scopus 로고
    • For selected studies of biologically active compounds bearing a trans-β- aminoether motif, see: (a) Plouvier, B.; Beatch, G. N.; Jung, G. L.; Zolotoy, A.; Sheng, T.; Clohs, L.; Barrett, T. D.; Fedida, D.; Wang, W. Q.; Zhu, J. J.; Liu, Y.; Abraham, S.; Lynn, L.; Dong, Y.; Wall, R. A.; Walker, M. J. A. J. Med. Chem. 2007, 50, 2818.
    • For selected studies of biologically active compounds bearing a trans-β- aminoether motif, see: (a) Plouvier, B.; Beatch, G. N.; Jung, G. L.; Zolotoy, A.; Sheng, T.; Clohs, L.; Barrett, T. D.; Fedida, D.; Wang, W. Q.; Zhu, J. J.; Liu, Y.; Abraham, S.; Lynn, L.; Dong, Y.; Wall, R. A.; Walker, M. J. A. J. Med. Chem. 2007, 50, 2818.
  • 38
    • 33646560979 scopus 로고    scopus 로고
    • 3, see:(a) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
    • 3, see:(a) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
  • 40
    • 23844530814 scopus 로고    scopus 로고
    • With TMSCN: (c) Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
    • With TMSCN: (c) Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
  • 41
    • 35048832273 scopus 로고    scopus 로고
    • 3. In this case covalent activation of benzoylated aziridine by silylated phosphate was proposed: Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084.
    • 3. In this case covalent activation of benzoylated aziridine by silylated phosphate was proposed: Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084.
  • 42
    • 0037099465 scopus 로고    scopus 로고
    • Episulfonium ions are intermediates in numerous reactions but have not been exploited in the context of asymmetric catalysis; for a review, see: Fox, D. J, House, D, Warren, S. Angew. Chem, Int. Ed. 2002, 41, 2462
    • Episulfonium ions are intermediates in numerous reactions but have not been exploited in the context of asymmetric catalysis; for a review, see: Fox, D. J.; House, D.; Warren, S. Angew. Chem., Int. Ed. 2002, 41, 2462.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.