Regio- and stereoselective ring-opening reaction of 2,3-epoxy amines with organo-aluminum reagents leading to 2-substituted 3-amino alcohols

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6177-6180

  Liu, Changqing ^a   Hashimoto, Yukihiko ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; GLYCIDOL;

ALKYLATION; ARTICLE; CONFORMATIONAL TRANSITION; MOLECULAR INTERACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0030593627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01341-X     Document Type: Article

References (18)

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3. c) Behrens, C.H.; Sharpless, K.B. Aldrichimica Acta 1983, 16, 67-79.
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5. 2. a) Johnson, R.A.; Sharpless, K.B. Comprehensive Organic Synthesis, ed by Trost, B.M.; Fleming, I., Pergamon Press: Oxford, 1991, Vol. 7, pp. 389-436.
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7. c) Pfenniger, A. Synthesis, 1986, 89-116;
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11. b) Liu, Q.; Marchington, A.P.; Boden, N.; Rayner, C.M. Synlett 1995, 1037-1039.
12. c) Westwell, A.d.; Thornton-Pett, M.; Rayner, C.M. J. Chem. Soc., Perkin Trans. 1 1995, 847-859.
13. d) Liu, Q.; Simms, M.J.; Boden, N.; Rayner, C.M. J. Chem. Soc., Perkin Trans. 1 1994, 1363-1365.
14. 4. Liu, C.; Hashimoto, Y.; Kudo, K.; Saigo, K. Bull. Chem. Soc. Jpn. 1996, 69, in press.
15. 1H NMR and IR spectra were obtained for all of the products listed in Table 1.
16. 6. The argument for the intramolecular nucleophilic attack is based on Rayner's finding that an intermolecular nucleophilic attack to an aziridinium ion occurred preferentially at the C-1 (see ref. 3d).
17. 7. See, for example, a) Glasby, J.S. Encyclopaedia of Antibiotics, 2nd Edn, Wiley: New York, 1979.
18. b) Rosenthal, G.A. Plant Nonprotein Amino and Imino Acids, Academic Press: New York, 1982.