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Volumn 52, Issue 46, 1996, Pages 14533-14542

Facile syntheses of α-bromo-α-silyl ketones and α-bromoacylsilanes from tert-butyldimethylsilyldibromomethane and carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANOBROMINE DERIVATIVE; SILANE DERIVATIVE;

EID: 0030580396     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00898-8     Document Type: Article
Times cited : (7)

References (42)
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    • Trost, B. M., Fleming, I., Pattenden, G. Eds.; Pergamon Press: New York Chapter, 3.3. Similar 1,2-migration of hydrogen has been reported. See ref. 1d and 1e
    • 6. Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G. Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 3.3 pp. 733-775. Similar 1,2-migration of hydrogen has been reported. See ref. 1d and 1e.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733-775
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    • 7. For a reductive formation of enolate from α-haloketone with various organometallic compounds, see: Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463-464.
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    • 8. A regioselective enolate formation from trimethylsilylmethyl ketones has been reported. Matsuda, I.; Okada, H.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1984, 25, 3879-3882.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3879-3882
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    • note
    • 9. The use of heptanal in place of benzaldehyde afforded a trace amount of the corresponding monosilyl ether of 2-acyl-1,3-diol.
  • 35
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    • 10. Yamamoto, K.; Tomo, Y.; Suzuki, S.; Tetrahedron Lett. 1980, 21, 2861-2864; Larcheveque, M.; Debal, A. J. Chem. Soc. Chem. Commun. 1981, 877-878; Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385-3386.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 2861-2864
    • Yamamoto, K.1    Tomo, Y.2    Suzuki, S.3
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    • 10. Yamamoto, K.; Tomo, Y.; Suzuki, S.; Tetrahedron Lett. 1980, 21, 2861-2864; Larcheveque, M.; Debal, A. J. Chem. Soc. Chem. Commun. 1981, 877-878; Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385-3386.
    • (1981) J. Chem. Soc. Chem. Commun. , pp. 877-878
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    • 10. Yamamoto, K.; Tomo, Y.; Suzuki, S.; Tetrahedron Lett. 1980, 21, 2861-2864; Larcheveque, M.; Debal, A. J. Chem. Soc. Chem. Commun. 1981, 877-878; Larson, G. L.; de Kaifer, C. F.; Seda, R.; Torres, L. E.; Ramirez, J. R. J. Org. Chem. 1984, 49, 3385-3386.
    • (1984) J. Org. Chem. , vol.49 , pp. 3385-3386
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    • note
    • 2 also gave only (E)-10d in 90 % yield. The exclusive formation of (E)-isomer might be attributed to the isomerization of (Z)-isomer into (E)-isomer under the acidic reaction conditions.
  • 39
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    • note
    • 14
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    • 13. For the nomenclature of threo and erythro, see: Noyori; R; Nishida, H. J. Am. Chem. Soc. 1981, 103, 2106-2108.
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    • note
    • 15. Butyllithium was not so effective as sec-BuLi for the formation of enolate in one-pot procedure.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.