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Volumn 3, Issue 10, 2001, Pages 1575-1577

Efficient Asymmetric Synthesis of α-Trifluoromethyl-Substituted Primary Amines via Nucleophilic 1,2-Addition to Trifluoroacetaldehyde SAMP- or RAMP-Hydrazone

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EID: 0000392742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015869g     Document Type: Article
Times cited : (71)

References (48)
  • 3
    • 0032512020 scopus 로고    scopus 로고
    • (b) Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; Ramachandran, P. V., Ed.; American Chemical Society, Washington, DC, 1999. Iseki, K. Tetrahedron 1998, 54, 13887.
    • (1998) Tetrahedron , vol.54 , pp. 13887
    • Iseki, K.1
  • 7
    • 0041705482 scopus 로고    scopus 로고
    • In ref 1a
    • (d) Mikami, K.; Yajima, T. In ref 1a, p 557. (e) Ramachandran, P. V.; Brown, H. C. In ref 1b, p 22.
    • Mikami, K.1    Yajima, T.2
  • 16
    • 0035793282 scopus 로고    scopus 로고
    • (g) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem. 2001, 113, 609; Angew. Chem., Int. Ed. 2001, 40, 589.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 589
  • 17
    • 0042205955 scopus 로고    scopus 로고
    • In ref 1a
    • For a review on functionalized α-trifluoromethylated amines using the sulfinyl or 1-phenylethyl group as a chiral auxiliary, see: (h) Bravo, P.; Zanda, M. In ref 1a, p 107.
    • Bravo, P.1    Zanda, M.2
  • 24
  • 28
    • 0000434949 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • (b) Enders, D. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York. 1984; Vol. 3. p 275.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 275
    • Enders, D.1
  • 31
    • 0041705479 scopus 로고    scopus 로고
    • note
    • Trifluoroacetaldehyde SAMP-hydrazone is much more stable than trifluoroacetaldehyde imines. Therefore in contrast the hydrazone can be purified by flash column chromatography.
  • 32
    • 0042205953 scopus 로고    scopus 로고
    • note
    • 2O (10/1) gave 3a in 79% yield.
  • 35
    • 0043208237 scopus 로고    scopus 로고
    • note
    • Details of X-ray structure analysis will be described in a full paper.
  • 44
    • 0001651037 scopus 로고    scopus 로고
    • (h) Kadota, I.; Park, J.-Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 841. Friestad, G. K.; Qin, J. J. Am. Chem. Soc. 2000, 122, 8329.
    • (2000) Am. Chem. Soc. , vol.122 , pp. 8329
    • Friestad, G.K.1    Qin, J.J.2
  • 46
    • 0042707076 scopus 로고    scopus 로고
    • note
    • 2O (5/1) as the eluent, affording 5a in 87% yield.
  • 48
    • 0039592749 scopus 로고    scopus 로고
    • 2, see: Fernández, R.; Ferrete, A.; Lassaletta, J. M.; Llera, J. M.; Monge, A. Angew. Chem. 2000, 112, 3015; Angew. Chem., Int. Ed. 2000, 39, 2893.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2893


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.