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Volumn 64, Issue 8, 1999, Pages 2843-2846

Preparation and synthetic applications of enantiopure (2S,3S)- or (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amines

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOMETHYL 1,2 EPOXYALKAN 3 AMINE DERIVATIVE; ALKANE DERIVATIVE; AMINE; HYDROGEN; LITHIUM; UNCLASSIFIED DRUG;

EID: 0033574487     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823590     Document Type: Article
Times cited : (23)

References (34)
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    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 7
    • For general reviews of the reactivity of 2,3-epoxy alcohols, see: (a) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 7.
    • (1985) Asymmetric Synthesis , vol.5
    • Rossiter, B.E.1
  • 2
    • 0000830825 scopus 로고
    • For other recent synthetic applications of 2,3-epoxy alcohols, see
    • (b) Hanson, R. M. Chem. Rev. 1991, 91, 437. For other recent synthetic applications of 2,3-epoxy alcohols, see:
    • (1991) Chem. Rev. , vol.91 , pp. 437
    • Hanson, R.M.1
  • 3
    • 0029126720 scopus 로고
    • For the reactivity of α,β-epoxy ketones, see
    • (c) Bonini, C.; Federici, C.; Rossi, L.; Righi, G. J. Org. Chem. 1995, 60, 4803. For the reactivity of α,β-epoxy ketones, see:
    • (1995) J. Org. Chem. , vol.60 , pp. 4803
    • Bonini, C.1    Federici, C.2    Rossi, L.3    Righi, G.4
  • 4
    • 33845374408 scopus 로고
    • For synthetic applications of vinyloxiranes, see
    • (d) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596. For synthetic applications of vinyloxiranes, see:
    • (1986) J. Org. Chem. , vol.51 , pp. 2596
    • Molander, G.A.1    Hahn, G.2
  • 5
    • 0037629474 scopus 로고
    • For the reactivity of α,β-epoxy silanes, see
    • (e) Molander, G. A.; La Belle, B. E.; Hahn, G. J. Org. Chem. 1986, 51, 5259. For the reactivity of α,β-epoxy silanes, see:
    • (1986) J. Org. Chem. , vol.51 , pp. 5259
    • Molander, G.A.1    La Belle, B.E.2    Hahn, G.3
  • 6
    • 85037455306 scopus 로고
    • For synthetic applications of α-amino epoxides, see
    • (f) Gorzynski, J. Synthesis 1984, 629. For synthetic applications of α-amino epoxides, see:
    • (1984) Synthesis , pp. 629
    • Gorzynski, J.1
  • 18
    • 0010555511 scopus 로고
    • A multistep synthesis of chiral substituted epihalohydrins has been described via Sharpless epoxidation, treatment with tosyl chloride, and further displacement by chloride or bromide: Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414.
    • (1990) J. Org. Chem. , vol.55 , pp. 1414
    • Discordia, R.P.1    Dittmer, D.C.2
  • 19
    • 0040131254 scopus 로고
    • For other recent applications of epoxides, see
    • (a) For general applications of epoxides in organic synthesis, see: Behrens, C. H.; Sharpless, K. B. Aldrichimica Acta 1993, 16, 67. For other recent applications of epoxides, see:
    • (1993) Aldrichimica Acta , vol.16 , pp. 67
    • Behrens, C.H.1    Sharpless, K.B.2
  • 30
    • 0345051452 scopus 로고    scopus 로고
    • note
    • In the case of bromomethyl ketones, the reaction was slowly allowed to warm to room temperature overnight to avoid the formation of a mixture of regioisomers due to the small difference between bromine and iodide as leaving groups.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.