메뉴 건너뛰기




Volumn 61, Issue 20, 1996, Pages 6901-6905

Utilization of tetrabutylammonium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001443339     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960922d     Document Type: Article
Times cited : (155)

References (32)
  • 1
    • 3643105529 scopus 로고
    • Schlosser, M., Ed.; J. Wiley & Sons: New York, Chapters 1 and 4 and references cited therein
    • Schlosser, M.; Lipshutz, B. H. In Organometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: New York, 1994; Chapters 1 and 4 and references cited therein.
    • (1994) Organometallics in Synthesis
    • Schlosser, M.1    Lipshutz, B.H.2
  • 9
    • 3643097108 scopus 로고    scopus 로고
    • note
    • Some of the TMS ethers resulting from condensation are hydrolytically unstable. For these products, the standard workup procedures involving exposure of the crude products to dilute acid resulted in removal of the TMS ether.
  • 10
    • 3643061685 scopus 로고    scopus 로고
    • note
    • In a control experiment, treatment of hexanal with TBAT under the described conditions in the absence of allyltrimethylsilane did not produce aldol products.
  • 14
    • 0001226919 scopus 로고
    • (d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4081
    • Kira, M.1    Kobayashi, M.2    Sakurai, H.3
  • 15
    • 0001226919 scopus 로고
    • and references cited therein
    • (d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
    • (1990) Synlett , pp. 1
    • Sakurai, H.1
  • 18
    • 84972899517 scopus 로고
    • This is the first example of fluoride-initiated intermolecular coupling between allyltrimethylsilane and an imine derivative. For an example of an alkoxide-induced reaction between an imine and a benzylsilane derivative, see: Shimizu, S.; Ogata, M. Synth.Commun. 1989, 19, 2219.
    • (1989) Synth.Commun. , vol.19 , pp. 2219
    • Shimizu, S.1    Ogata, M.2
  • 23
    • 0002282172 scopus 로고
    • and references cited therein
    • (e) Yamamoto, Y. Alrichimica Acta 1987, 20, 45 and references cited therein.
    • (1987) Alrichimica Acta , vol.20 , pp. 45
    • Yamamoto, Y.1
  • 29
    • 0001453658 scopus 로고
    • For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
    • (1995) J. Org. Chem. , vol.60 , pp. 5366
    • Jin, J.1    Smith, D.T.2    Weinreb, S.M.3
  • 30
    • 0028125319 scopus 로고
    • For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
    • (1994) J. Am Chem. Soc. , vol.116 , pp. 9789
    • Borzilleri, R.M.1    Weinreb, S.M.2    Parzez, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.