Amine-catalyzed addition of azide ion to α,β-unsaturated carbonyl compounds

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1107-1109

  Guerin, David J ^a   Horstmann, Thomas E ^a   Miller, Scott J ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIDE; ION; KETONE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINES; AZIDES; CATALYSIS; IONS; KETONES;

EID: 0033533638     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9909076     Document Type: Article

References (20)

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7. (b) See also: ref 1.
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13. 3, see: Chung, B. Y.; Park, Y. S.; Cho, I. S.; Hyun, B. C. Bull. Korean Chem. Soc. 1988, 9, 269-270.
14. 3, see: Magnus, P.; Lacour, J. Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406-3418.
15. 3N.
16. f, and combustion analysis. Supporting Information for this Letter is available.
17. Caution: Organic azides are potentially explosive compounds and should be handled with great care. We encountered no explosive behavior during these studies, however. In addition, differential scanning calorimetry (DSC) was performed on compounds 2, 6, and 13 at Science Resources, Inc. (Evansville, IN). In each case, the thermochemical transitions occurred at ≥ 130°C. Full details of these measurements are reported in the Supporting Information (pp SI-9-SI-13).
18. 3 and related azides, see: Bretherick, L. Handbook of Reactive Chemical Hazards; Butterworth: London, 1975; pp 775-776.
19. For the preparation of this catalyst, see: Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org, Chem, 1998, 63, 6784-6785.
20. α-Azido ketones may also be converted to an α-amino acid. For example, see: Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111-113.