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Volumn 8, Issue 25, 2006, Pages 5737-5740

Stereocontrolled route to vicinal diamines by [3.3] sigmatropic rearrangement of allyl cyanate: Asymmetric synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIAMINOBUTANOIC ACID; 2,3-DIAMINOBUTANOIC ACID; ACETALDEHYDE; ALLYL COMPOUND; ALLYL ISOCYANATE; AMINOBUTYRIC ACID DERIVATIVE; DIAMINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ISOCYANIC ACID DERIVATIVE; KETONE; PHOSPHONIC ACID DERIVATIVE; REDUCING AGENT; UNCLASSIFIED DRUG;

EID: 33846311745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0621102     Document Type: Article
Times cited : (29)

References (36)
  • 1
    • 0032538362 scopus 로고
    • For a review on the synthesis of vicinal diamines, see: a
    • For a review on the synthesis of vicinal diamines, see: (a) Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1988, 37, 2580-2627.
    • (1988) Angew. Chem., Int. Ed , vol.37 , pp. 2580-2627
    • Lucet, D.1    Gall, T.L.2    Mioskowski, C.3
  • 2
    • 3242721636 scopus 로고    scopus 로고
    • For recent examples on the synthesis of vicinal diamines, see: b
    • For recent examples on the synthesis of vicinal diamines, see: (b) Ooi, T.; Kameda, M.; Fuji, J.; Maruoka, K. Org. Lett. 2004, 6, 2397-2399.
    • (2004) Org. Lett , vol.6 , pp. 2397-2399
    • Ooi, T.1    Kameda, M.2    Fuji, J.3    Maruoka, K.4
  • 8
    • 0033529724 scopus 로고    scopus 로고
    • For a comprehensive summary of literature related to the synthesis of α,β-diamino acids, see: a
    • For a comprehensive summary of literature related to the synthesis of α,β-diamino acids, see: (a) Luo, Y.; Blaskovich, M. A.; Lajoie, G. A. J. Org. Chem. 1999, 64, 6106-6111.
    • (1999) J. Org. Chem , vol.64 , pp. 6106-6111
    • Luo, Y.1    Blaskovich, M.A.2    Lajoie, G.A.3
  • 10
    • 4344680460 scopus 로고    scopus 로고
    • For a recent report on the asymmetric synthesis of α,β-diamino acids, see: c
    • For a recent report on the asymmetric synthesis of α,β-diamino acids, see: (c) Davis, F. A.; Deng, J. Org. Lett. 2004, 6, 2789-2792.
    • (2004) Org. Lett , vol.6 , pp. 2789-2792
    • Davis, F.A.1    Deng, J.2
  • 19
    • 0000269034 scopus 로고    scopus 로고
    • 1,2-Asymmetric induction of a similar α-oxygenated enone using LAH was reported by Overman: (a) Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2355-2358.
    • 1,2-Asymmetric induction of a similar α-oxygenated enone using LAH was reported by Overman: (a) Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2355-2358.
  • 20
  • 25
    • 33846291147 scopus 로고    scopus 로고
    • Anh, N. T.; Eisenstein, O. Nouv. J. Chem. 1976, 61-70. See also refs 10b and 11.
    • (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chem. 1976, 61-70. See also refs 10b and 11.
  • 30
    • 33748734782 scopus 로고    scopus 로고
    • Addition of tributyltin alkoxide enhanced the efficiency of this in situ trapping isocyanate. See
    • Addition of tributyltin alkoxide enhanced the efficiency of this in situ trapping isocyanate. See: Ichikawa, Y.; Osada, M.; Ohtani, I.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1997, 1449-1455.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1449-1455
    • Ichikawa, Y.1    Osada, M.2    Ohtani, I.3    Isobe, M.4
  • 31
    • 0000192963 scopus 로고
    • It should be noted that because the prolonged reaction time of this oxidative deprotection resulted in the formation of enone i, it was necessary to perform a workup immediately after checking the consumption of starting material by TLC analysis, diagram presented
    • Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888. It should be noted that because the prolonged reaction time of this oxidative deprotection resulted in the formation of enone i, it was necessary to perform a workup immediately after checking the consumption of starting material by TLC analysis. (diagram presented)
    • (1982) Tetrahedron Lett , vol.23 , pp. 885-888
    • Oikawa, Y.1    Yoshioka, T.2    Yonemitsu, O.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.