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Volumn 131, Issue 10, 2009, Pages 3490-3492

Observation of direct sulfenium and selenenium group transfer from thiiranium and seleniranium ions to alkenes

Author keywords

[No Author keywords available]

Indexed keywords

EQUILIBRIUM POSITIONS; GROUP TRANSFER; NMR SPECTRUM; RELATIVE STABILITIES; ROOM TEMPERATURE; SELENIDES; SILVER CHLORIDES; STEREOSPECIFIC; THREE-MEMBERED RINGS;

EID: 69949112440     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900187y     Document Type: Article
Times cited : (113)

References (61)
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    • An important exception is the enantioselective functionalization of aldehydes with sulfur and selenium electrophiles, catalyzed by chiral amines (via their enamines, a) Marigo, M, Wabnitz, T. C, Fielenbach, D, Jørgensen, K. A. Angew. Chem, Int. Ed. 2005, 44, 794-797
    • An important exception is the enantioselective functionalization of aldehydes with sulfur and selenium electrophiles, catalyzed by chiral amines (via their enamines). (a) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794-797.
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    • (d) Zhao, G.-L.; Rios, R.; Vesely, J.; Eriksson, L.; Cordova, A. Angew. Chem., Int. Ed. 2008, 47, 8468-8472. See also:
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    • Rayner, C. M. In Organosulfur Chemistry: Synthetic Aspects; Bullman- Page, P., Ed.; Academic Press: London, 1995; pp 89-131.
    • (a) Rayner, C. M. In Organosulfur Chemistry: Synthetic Aspects; Bullman- Page, P., Ed.; Academic Press: London, 1995; pp 89-131.
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    • (c) Schmid, G. H.; Garratt, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, pp 854-866.
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    • (a) Borodkin, G. I.; Gatilov, Y. V.; Chernyak, E. I.; Shubin, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 2826; 1985, 34, 2622 (Engl. Transl.).
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    • Borodkin, G. I.; Chernyak, E. I.; Shakirov, M. M.; Gatilov, Y. V.; Rybalova, T. V.; Shubin, V. G. Zh. Org. Khim. 1990, 26, 1163-1179; 1990, 26, 1002-1017 (Engl. Transl.).
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    • Toshimitsu, A.; Hayashi, G.; Terao, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1986, 343-347. (e) Toshimitsu, A.; Ito, M.; Uemura, S. J. Chem. Soc., Chem. Commun. 1989, 530-531.
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  • 52
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    • Lucchini and co-workers have shown that chiral, nonracemic thiiranium ions generated in situ by sulfenium ion transfer can be trapped at low temperature with good enantioselectivity; see ref 7k
    • Lucchini and co-workers have shown that chiral, nonracemic thiiranium ions generated in situ by sulfenium ion transfer can be trapped at low temperature with good enantioselectivity; see ref 7k.
  • 59
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    • The thiiranium substrate scope was limited to those compounds that could be prepared cleanly and differentiated from each other by 1H NMR analysis if present in a mixture. The S-Ph analogues of thiiranium ions 5 and 6 were unstable at the temperatures required to perform our investigations. Thiiranium analogues of cyclohexyl seleniranium ions 9 and 10 have been reported in the literature but are not stable above-40 °C
    • The thiiranium substrate scope was limited to those compounds that could be prepared cleanly and differentiated from each other by 1H NMR analysis if present in a mixture. The S-Ph analogues of thiiranium ions 5 and 6 were unstable at the temperatures required to perform our investigations. Thiiranium analogues of cyclohexyl seleniranium ions 9 and 10 have been reported in the literature but are not stable above-40 °C.
  • 60
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    • The relative thermodynamic ground-state energies of seleniranium ions 9 and 13 correspond nicely to the expected relative energies for strained cis-bicyclo[ 4.1.0]heptane and cis-bicyclo[6.1.0]nonane, respectively. Chang, S.-J.; McNally, D.; Shary-Tehrany, S.; Hickey, J.; Boyd, R. H. J. Am. Chem. Soc. 1970, 92, 3109-3118.
    • The relative thermodynamic ground-state energies of seleniranium ions 9 and 13 correspond nicely to the expected relative energies for strained cis-bicyclo[ 4.1.0]heptane and cis-bicyclo[6.1.0]nonane, respectively. Chang, S.-J.; McNally, D.; Shary-Tehrany, S.; Hickey, J.; Boyd, R. H. J. Am. Chem. Soc. 1970, 92, 3109-3118.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.