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Volumn 5, Issue 16, 2003, Pages 2963-2965

Photolysis of diacyl peroxides: A radical-based approach for the synthesis of functionalized amino acids

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; LEUCINE; PEROXIDE;

EID: 0141631627     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035125y     Document Type: Article
Times cited : (36)

References (28)
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    • For leading references, see: (a) Ryzhkov, L. R. J. Org. Chem. 1996, 61, 2801-2808. (b) Fujimori, K.; Hirose, Y.; Oae, S. J. Chem. Soc., Perkin Trans. 2 1996, 405-412. (c) Radziszewski, J. G.; Nimlos, M. R.; Winter, P. R.; Ellison, G. B. J. Am. Chem. Soc. 1996, 118, 7400-7401. (d) Linhardt, R. J.; Murr, B. L.; Montgomery, E.; Osby, J.; Sherbine, J. J. Org. Chem. 1982, 47, 2242-2251.
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    • Ryzhkov, L.R.1
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    • For leading references, see: (a) Ryzhkov, L. R. J. Org. Chem. 1996, 61, 2801-2808. (b) Fujimori, K.; Hirose, Y.; Oae, S. J. Chem. Soc., Perkin Trans. 2 1996, 405-412. (c) Radziszewski, J. G.; Nimlos, M. R.; Winter, P. R.; Ellison, G. B. J. Am. Chem. Soc. 1996, 118, 7400-7401. (d) Linhardt, R. J.; Murr, B. L.; Montgomery, E.; Osby, J.; Sherbine, J. J. Org. Chem. 1982, 47, 2242-2251.
    • (1996) J. Chem. Soc., Perkin Trans. 2 , pp. 405-412
    • Fujimori, K.1    Hirose, Y.2    Oae, S.3
  • 3
    • 0029777487 scopus 로고    scopus 로고
    • For leading references, see: (a) Ryzhkov, L. R. J. Org. Chem. 1996, 61, 2801-2808. (b) Fujimori, K.; Hirose, Y.; Oae, S. J. Chem. Soc., Perkin Trans. 2 1996, 405-412. (c) Radziszewski, J. G.; Nimlos, M. R.; Winter, P. R.; Ellison, G. B. J. Am. Chem. Soc. 1996, 118, 7400-7401. (d) Linhardt, R. J.; Murr, B. L.; Montgomery, E.; Osby, J.; Sherbine, J. J. Org. Chem. 1982, 47, 2242-2251.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7400-7401
    • Radziszewski, J.G.1    Nimlos, M.R.2    Winter, P.R.3    Ellison, G.B.4
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    • For leading references, see: (a) Ryzhkov, L. R. J. Org. Chem. 1996, 61, 2801-2808. (b) Fujimori, K.; Hirose, Y.; Oae, S. J. Chem. Soc., Perkin Trans. 2 1996, 405-412. (c) Radziszewski, J. G.; Nimlos, M. R.; Winter, P. R.; Ellison, G. B. J. Am. Chem. Soc. 1996, 118, 7400-7401. (d) Linhardt, R. J.; Murr, B. L.; Montgomery, E.; Osby, J.; Sherbine, J. J. Org. Chem. 1982, 47, 2242-2251.
    • (1982) J. Org. Chem. , vol.47 , pp. 2242-2251
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    • Warning: Although larger diacyl peroxides cannot be detonated, small diacyl peroxides with ≤7 carbons on each side (e.g., diacetyl peroxide) can be explosive and hazardous. As scrambling of acyl groups can occur during preparation, coupling of small acyl groups (e.g., acetyl) should be avoided. For example of scrambling, see: Staab, H. A.; Rohr, W.; Graf, F. Chem. Ber. 1965, 98, 1128-1133.
    • (1965) Chem. Ber. , vol.98 , pp. 1128-1133
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    • For selected references on amino acid synthesis, see: (a) Williams, R. M. In Organic Chemistry Series, Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi S. J. Am. Chem. Soc. 2000, 122, 762-766.
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    • For selected references on amino acid synthesis, see: (a) Williams, R. M. In Organic Chemistry Series, Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi S. J. Am. Chem. Soc. 2000, 122, 762-766.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9375-9376
    • Burk, M.J.1    Gross, M.F.2    Martinez, J.P.3
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    • 0031047509 scopus 로고    scopus 로고
    • For selected references on amino acid synthesis, see: (a) Williams, R. M. In Organic Chemistry Series, Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi S. J. Am. Chem. Soc. 2000, 122, 762-766.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 656-673
    • Myers, A.G.1    Gleason, J.L.2    Yoon, T.3    Kung, D.W.4
  • 15
    • 0031055591 scopus 로고    scopus 로고
    • For selected references on amino acid synthesis, see: (a) Williams, R. M. In Organic Chemistry Series, Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi S. J. Am. Chem. Soc. 2000, 122, 762-766.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 445-446
    • Petasis, N.A.1    Zavialov, I.A.2
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    • 0034624418 scopus 로고    scopus 로고
    • For selected references on amino acid synthesis, see: (a) Williams, R. M. In Organic Chemistry Series, Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi S. J. Am. Chem. Soc. 2000, 122, 762-766.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 762-766
    • Ishitani, H.1    Komiyama, S.2    Hasegawa, Y.3    Kobayashi, S.4
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    • note
    • 2, with irradiation directly from above.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.