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Volumn 132, Issue 44, 2010, Pages 15752-15765

Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions

Author keywords

[No Author keywords available]

Indexed keywords

BINAPHTHALENES; CHEMICAL YIELDS; CONFIGURATIONAL STABILITY; CRITICAL CHALLENGES; ELECTROPHILES; ENANTIOSELECTIVE; LEWIS BASE; LEWIS BASIS; MECHANISTIC STUDIES; METHANE SULFONIC ACID; RACEMIZATION PATHWAY; SELENIUMS ( II); SUCCINIMIDE; SYSTEMATIC INVESTIGATIONS; UNACTIVATED OLEFINS; UNSATURATED ALCOHOLS;

EID: 78649735581     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106837b     Document Type: Article
Times cited : (146)

References (123)
  • 3
    • 78649723674 scopus 로고
    • Ed.; Wiley: New York,; Chap. 1 and 2
    • Liotta, D., Ed. Organoselenium Chemistry; Wiley: New York, 1987; Chap. 1 and 2, pp 1-163.
    • (1987) Organoselenium Chemistry , pp. 1-163
    • Liotta, D.1
  • 44
    • 69949112440 scopus 로고    scopus 로고
    • Ongoing work in these laboratories involves the development of equally challenging catalytic, enantioselective thiofunctionalization of olefins. For preliminary mechanistic work toward this goal, see
    • Ongoing work in these laboratories involves the development of equally challenging catalytic, enantioselective thiofunctionalization of olefins. For preliminary mechanistic work toward this goal, see: Denmark, S. E., Collins, W. R., and Cullen, M. D. J. Am. Chem. Soc. 2009, 131, 3490-3491
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3490-3491
    • Denmark, S.E.1    Collins, W.R.2    Cullen, M.D.3
  • 70
    • 78649730337 scopus 로고    scopus 로고
    • Ph.D. thesis, University of Illinois, Urbana-Champaign.
    • Collins, W. R. Ph.D. thesis, University of Illinois, Urbana-Champaign, 2009.
    • (2009)
    • Collins, W.R.1
  • 71
    • 78649721888 scopus 로고    scopus 로고
    • Alternatively, as in Wirth's system, capture could be stereodetermining and cannot be ruled out at this time.
    • Alternatively, as in Wirth's system, capture could be stereodetermining and cannot be ruled out at this time.
  • 82
    • 78649730121 scopus 로고    scopus 로고
    • starting material) × 100%] provides a convenient method for describing the conservation of configurational purity of a reaction.
    • starting material) × 100%] provides a convenient method for describing the conservation of configurational purity of a reaction.
  • 91
    • 78649756593 scopus 로고    scopus 로고
    • The er's of 25a and 25f were checked against the racemates and were found to be 95:5 and 96:4, respectively. Therefore, it is reasonable to assume that the er's of 25b-e and 25g are not significantly different than that of the starting epoxide 23.
    • The er's of 25a and 25f were checked against the racemates and were found to be 95:5 and 96:4, respectively. Therefore, it is reasonable to assume that the er's of 25b-e and 25g are not significantly different than that of the starting epoxide 23.
  • 94
    • 78649752443 scopus 로고    scopus 로고
    • A >100% es was observed for the reactions for which es is reported as >99%. This is likely because the er's of carbonate in these cases were higher than the assumed er (93:7).
    • A >100% es was observed for the reactions for which es is reported as >99%. This is likely because the er's of carbonate in these cases were higher than the assumed er (93:7).
  • 95
    • 78649746571 scopus 로고    scopus 로고
    • 1H NMR spectroscopic analysis of the isolated product showed approximately a 2:1 ratio of 28f: 31.
    • 1H NMR spectroscopic analysis of the isolated product showed approximately a 2:1 ratio of 28f: 31.
  • 99
    • 78649729888 scopus 로고    scopus 로고
    • 1H NMR spectra of unpurified reaction mixtures.
    • 1H NMR spectra of unpurified reaction mixtures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.