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Volumn 12, Issue 21, 2010, Pages 5072-5074

γ-oxygenation of α,β-unsaturated esters by vinylogous O-nitroso mukaiyama aldol reaction

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EID: 78049518498     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1021433     Document Type: Article
Times cited : (28)

References (64)
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    • For leading references, see
    • For leading references, see
  • 9
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    • For reviews of O -nitroso aldol reactions, see
    • For reviews of O -nitroso aldol reactions, see
  • 16
    • 0037613521 scopus 로고    scopus 로고
    • correction J. Am. Chem. Soc. 2004, 126, 6498
    • Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039; correction J. Am. Chem. Soc. 2004, 126, 6498.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6038-6039
    • Momiyama, N.1    Yamamoto, H.2
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    • For examples, see
    • For examples, see
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    • 3). See
    • 3). See
  • 41
    • 78049507121 scopus 로고    scopus 로고
    • While the reactions were typically carried out in one pot, the γ-aminoxy-α,β-unsaturated ester intermediates could be isolated and characterized. See Supporting Information for full characterization of the γ-aminoxy-α,β-unsaturated ester intermediate (7) of Table 2, entry 14
    • While the reactions were typically carried out in one pot, the γ-aminoxy-α,β-unsaturated ester intermediates could be isolated and characterized. See Supporting Information for full characterization of the γ-aminoxy-α,β-unsaturated ester intermediate (7) of Table 2, entry 14.
  • 42
    • 78049519471 scopus 로고    scopus 로고
    • For some reviews, see
    • For some reviews, see
  • 46
    • 78049508367 scopus 로고    scopus 로고
    • One of the reviewers raised an interesting possibility that the reaction proceeds by an initial N -nitroso aldol reaction followed by a [2,3]-sigmatropic rearrangement of the resulting α- N -phenylhydroxyamino-β,γ- unsaturated ester to give the γ-aminoxy-α,β-unsaturated ester intermediate. While we cannot rule out this possibility, related studies of nitroso aldol reactions with aldehydes and ketones suggest that O - instead of N -nitroso aldol products are likely to be preferred under the current reaction conditions as a result of the difference in basicities of the oxygen and nitrogen atoms. See ref 2a and
    • One of the reviewers raised an interesting possibility that the reaction proceeds by an initial N -nitroso aldol reaction followed by a [2,3]-sigmatropic rearrangement of the resulting α- N -phenylhydroxyamino-β,γ- unsaturated ester to give the γ-aminoxy-α,β-unsaturated ester intermediate. While we cannot rule out this possibility, related studies of nitroso aldol reactions with aldehydes and ketones suggest that O-instead of N -nitroso aldol products are likely to be preferred under the current reaction conditions as a result of the difference in basicities of the oxygen and nitrogen atoms. See ref 2a and
  • 48
    • 78049517950 scopus 로고    scopus 로고
    • For leading references of N -nitroso aldol reactions, see
    • For leading references of N -nitroso aldol reactions, see
  • 57
    • 78049507530 scopus 로고    scopus 로고
    • For some reviews
    • For some reviews
  • 64
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    • Abstracts of Papers, 25th Terupen, Seiyu oyobi Koryo ni kansuru Toronkai, Yamaguchi, Oct, p
    • Ichimura, N.; Matsuura, Y.; Kato, Y. Abstracts of Papers, 25th Terupen, Seiyu oyobi Koryo ni kansuru Toronkai, Yamaguchi, Oct 1981, p 18.
    • (1981) , pp. 18
    • Ichimura, N.1    Matsuura, Y.2    Kato, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.