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Volumn 9, Issue 23, 2007, Pages 4677-4680

Construction of three contiguous tertiary stereocenters from aziridines in one step

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EID: 36348932125     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7015302     Document Type: Article
Times cited : (25)

References (76)
  • 1
    • 30444441133 scopus 로고    scopus 로고
    • For recent reviews of Mannich reactions see: a
    • For recent reviews of Mannich reactions see: (a) Marques, M. M. B. Angew. Chem., Int. Ed. 2006, 45, 348.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 348
    • Marques, M.M.B.1
  • 3
  • 4
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfalz, A, Yamamoto, H, Eds, Springer-Verlag: Heidelberg
    • (d) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999.
    • (1999) Comprehensive Asymmetric Catalysis
  • 7
  • 21
    • 0036089366 scopus 로고    scopus 로고
    • For recent reviews on conjugate addition to nitroalkenes, see: a
    • For recent reviews on conjugate addition to nitroalkenes, see: (a) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
    • (2002) Eur. J. Org. Chem , pp. 1877
    • Berner, O.M.1    Tedeschi, L.2    Enders, D.3
  • 23
    • 0034612973 scopus 로고    scopus 로고
    • For a general review on enantioselective conjugate addition, see: c
    • For a general review on enantioselective conjugate addition, see: (c) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
    • (2000) Tetrahedron , vol.56 , pp. 8033
    • Sibi, M.P.1    Manyem, S.2
  • 24
    • 33748791724 scopus 로고    scopus 로고
    • For recent examples of asymmetric catalytic conjugate addition to nitroalkenes see: a
    • For recent examples of asymmetric catalytic conjugate addition to nitroalkenes see: (a) Palomo, C.; Vera, S.; Mielgo, A.; Gomez-Bengoa, E. Angew. Chem., Int. Ed. 2006, 45, 5984.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 5984
    • Palomo, C.1    Vera, S.2    Mielgo, A.3    Gomez-Bengoa, E.4
  • 39
    • 33748434728 scopus 로고    scopus 로고
    • For examples of the construction of three contiguous stereocenters adjacent to nitrogen atom in one step see: (a) Gui-Ling, Z, Cordova, A. Tetrahedron Lett. 2006, 47, 7417
    • For examples of the construction of three contiguous stereocenters adjacent to nitrogen atom in one step see: (a) Gui-Ling, Z.; Cordova, A. Tetrahedron Lett. 2006, 47, 7417.
  • 44
    • 33845230631 scopus 로고    scopus 로고
    • For our recent inroads in developing linchpin-based strategies, see
    • For our recent inroads in developing linchpin-based strategies, see: Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 14772.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14772
    • Hili, R.1    Yudin, A.K.2
  • 45
    • 77951231590 scopus 로고    scopus 로고
    • For recent reviews see: (a) Yudin, A. K, Ed, Wiley-VCH: Weinheim, Germany
    • For recent reviews see: (a) Yudin, A. K., Ed. Aziridines and Epoxides in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
    • (2006) Aziridines and Epoxides in Organic Synthesis
  • 47
  • 51
    • 23044453120 scopus 로고    scopus 로고
    • For examples of aziridine-ring-opening with C-nucleophiles see: (a) Hodgson, D. M, Fleming, M. J, Stanway, S. J. Org. Lett. 2005, 7, 3295
    • For examples of aziridine-ring-opening with C-nucleophiles see: (a) Hodgson, D. M.; Fleming, M. J.; Stanway, S. J. Org. Lett. 2005, 7, 3295.
  • 58
    • 0032578675 scopus 로고    scopus 로고
    • For synthesis of starting materials 1a and 1b see: (a) Ando, T.; Kano, D.; Minakata, S.; Rya, I.; Komatsu, M. Tetrahedron 1998, 54, 13485-13494.
    • For synthesis of starting materials 1a and 1b see: (a) Ando, T.; Kano, D.; Minakata, S.; Rya, I.; Komatsu, M. Tetrahedron 1998, 54, 13485-13494.
  • 59
    • 0042505113 scopus 로고    scopus 로고
    • For 1c: (b) Warnhoff, H.; Thiemig, H. A. Chem. Ber. 1985, 118, 4473-4485.
    • For 1c: (b) Warnhoff, H.; Thiemig, H. A. Chem. Ber. 1985, 118, 4473-4485.
  • 60
    • 0037178981 scopus 로고    scopus 로고
    • For 1d: (c) Mordini, A.; Russo, F.; Valachi, M.; Zani, L.; Degl'Innocenti, A.; Reginato, G. Tetrahedron, 2002, 58, 7153-7164.
    • For 1d: (c) Mordini, A.; Russo, F.; Valachi, M.; Zani, L.; Degl'Innocenti, A.; Reginato, G. Tetrahedron, 2002, 58, 7153-7164.
  • 61
    • 10644276146 scopus 로고    scopus 로고
    • For 2b: (d) Das, J.; Laxman Rao, C. V.; Sastry, T. V. R. S.; Roshaiah, M.; Sankar, P. G.; Khadeer, A.; Kumar, M. S.; Mallik, A.; Selvakumar, N.; Iqbal, J.; Trehan, S. Bioorg. Med. Chem. Lett. 2005, 12, 337-343. For 2c:
    • For 2b: (d) Das, J.; Laxman Rao, C. V.; Sastry, T. V. R. S.; Roshaiah, M.; Sankar, P. G.; Khadeer, A.; Kumar, M. S.; Mallik, A.; Selvakumar, N.; Iqbal, J.; Trehan, S. Bioorg. Med. Chem. Lett. 2005, 12, 337-343. For 2c:
  • 63
    • 3242764734 scopus 로고    scopus 로고
    • For 2d: (f) Zohdi, A. O.; Hussein, F.; Mohamed, G. S. Heteroat. Chem. 1999, 10, 508-516.
    • For 2d: (f) Zohdi, A. O.; Hussein, F.; Mohamed, G. S. Heteroat. Chem. 1999, 10, 508-516.
  • 64
    • 36349035656 scopus 로고    scopus 로고
    • For 2f: (g) Fischer, F. Can. J. Chem. 1978, 56, 3072, 3076.
    • For 2f: (g) Fischer, F. Can. J. Chem. 1978, 56, 3072, 3076.
  • 65
    • 36348960343 scopus 로고    scopus 로고
    • For 2g: Volovenko, Y. M.; Kupchevskaya, I. I.; Litvenko, S. V.; Babichev, F. S. Ukr. Khim. Zhurn. 1991, 54, 419-23.
    • For 2g: Volovenko, Y. M.; Kupchevskaya, I. I.; Litvenko, S. V.; Babichev, F. S. Ukr. Khim. Zhurn. 1991, 54, 419-23.
  • 66
    • 12944307318 scopus 로고    scopus 로고
    • For 2h: Danner, P.; Bauer, M.; Phukan, P.; Maier, M. E. Eur. J. Org. Chem. 2005, 2, 317-325.
    • For 2h: Danner, P.; Bauer, M.; Phukan, P.; Maier, M. E. Eur. J. Org. Chem. 2005, 2, 317-325.
  • 70
    • 0345871971 scopus 로고    scopus 로고
    • 4NX, X = Cl, Br, and I) were reported to be effective in aziridine ring-opening. The X-opened products were obtained. For instance, see: Fan, R. H.; Zhou, Y. G.; Zhang, W. X.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2004, 69, 335. This fact suggests that selection of the optimal quaternary ammonium salt counterion is important to avoid undesired products.
    • 4NX, X = Cl, Br, and I) were reported to be effective in aziridine ring-opening. The X-opened products were obtained. For instance, see: Fan, R. H.; Zhou, Y. G.; Zhang, W. X.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2004, 69, 335. This fact suggests that selection of the optimal quaternary ammonium salt counterion is important to avoid undesired products.
  • 71
    • 36349008894 scopus 로고    scopus 로고
    • Subjecting diastereomerically pure 3a to NaH/THF at 50°C for 30 min resulted in a 3:2 mixture of diastereomers.
    • Subjecting diastereomerically pure 3a to NaH/THF at 50°C for 30 min resulted in a 3:2 mixture of diastereomers.
  • 73
    • 4143049107 scopus 로고    scopus 로고
    • For recent reviews on asymmetric phase-transfer catalysis, see: a
    • For recent reviews on asymmetric phase-transfer catalysis, see: (a) O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506.
    • (2004) Acc. Chem. Res , vol.37 , pp. 506
    • O'Donnell, M.J.1
  • 75
    • 0002855131 scopus 로고    scopus 로고
    • Vogtle, F, Stoddart, J. F, Shibasaki, M, Eds, Wiley-VCH: Weinheim, Germany
    • (c) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000, p 123.
    • (2000) Stimulating Concepts in Chemistry , pp. 123
    • Shioiri, T.1    Arai, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.