Aziridinium ions from phenylglycinol - A new approach to the synthesis of chiral diamines

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4885-4888

  De Sousa, Simon E ^a   O'Brien, Peter ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; DIAMINE; PHENYLGLYCINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030987397     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01019-8     Document Type: Article

References (25)

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7. Current Aldrich Chemical Company Ltd prices: (R)-styrene oxide £32.50 per 5 g; (S)-styrene oxide £20.00 per 1 g.
8. Less reactive diamines require the use of a Lewis acid catalyst to promote epoxide ring opening. For example, lithium perchlorate-mediated ring opening of styrene oxide with diethylamine has been reported. In our hands, use of these conditions with styrene oxide and diethylamine, dimethylamine or dibenzylamine failed to generate high yields of the amino alcohol mixtures; our crude products were always contaminated with unreacted starting materials. See: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett., 1990, 31, 4661-4664; Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem., 1991, 56, 5939-5942; Augé, J.; Leroy, F. Tetrahedron Lett., 1996, 37, 7715-7716; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1, 1994, 2597-2601.
9. Less reactive diamines require the use of a Lewis acid catalyst to promote epoxide ring opening. For example, lithium perchlorate-mediated ring opening of styrene oxide with diethylamine has been reported. In our hands, use of these conditions with styrene oxide and diethylamine, dimethylamine or dibenzylamine failed to generate high yields of the amino alcohol mixtures; our crude products were always contaminated with unreacted starting materials. See: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett., 1990, 31, 4661-4664; Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem., 1991, 56, 5939-5942; Augé, J.; Leroy, F. Tetrahedron Lett., 1996, 37, 7715-7716; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1, 1994, 2597-2601.
10. Less reactive diamines require the use of a Lewis acid catalyst to promote epoxide ring opening. For example, lithium perchlorate-mediated ring opening of styrene oxide with diethylamine has been reported. In our hands, use of these conditions with styrene oxide and diethylamine, dimethylamine or dibenzylamine failed to generate high yields of the amino alcohol mixtures; our crude products were always contaminated with unreacted starting materials. See: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett., 1990, 31, 4661-4664; Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem., 1991, 56, 5939-5942; Augé, J.; Leroy, F. Tetrahedron Lett., 1996, 37, 7715-7716; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1, 1994, 2597-2601.
11. Less reactive diamines require the use of a Lewis acid catalyst to promote epoxide ring opening. For example, lithium perchlorate-mediated ring opening of styrene oxide with diethylamine has been reported. In our hands, use of these conditions with styrene oxide and diethylamine, dimethylamine or dibenzylamine failed to generate high yields of the amino alcohol mixtures; our crude products were always contaminated with unreacted starting materials. See: Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett., 1990, 31, 4661-4664; Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem., 1991, 56, 5939-5942; Augé, J.; Leroy, F. Tetrahedron Lett., 1996, 37, 7715-7716; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1, 1994, 2597-2601.
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19. In the absence of TBAI the reaction must be refluxed for 19 hours to reach completion.
20. 13C NMR spectroscopy and high resolution mass spectrometry.
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24. 2O as the solvent.
25. D -63.5 (c 1.6 in EtOH)} was obtained after Kugelrohr distillation.