Coupling of vinyl aziridines and phenyl isocyanate

Tetrahedron Letters

Volumn 49, Issue 27, 2008, Pages 4306-4309

  Zhang, Kainan ^a   Chopade, Pramod R ^a   Louie, Janis ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Imidazolidinone; N Heterocyclic carbene; Nickel; Oxazolidinone; Phenyl isocyanate; Tetrahydro 1,3 diazepin 2 one; Vinyl aziridine

Indexed keywords

HETEROCYCLIC COMPOUND; NICKEL; OXAZOLIDINONE DERIVATIVE; PHENYL ISOCYANATE; VINYLAZIRIDINE DERIVATIVE; VINYLIMIDAZOLIDINONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; THERMAL ANALYSIS;

EID: 44249090610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.121     Document Type: Article

References (15)

1. For the thermal reaction of an isocyanate and an aziridine, see:. Pfeil E., and Milzner K. Angew. Chem., Int. Ed. 5 (1966) 667
2. Nadir U.K., and Basu N. Tetrahedron Lett. 33 (1992) 7949
3. Munegumi T., Azumaya I., Kato T., Masu H., and Saito S. Org. Lett. 8 (2006) 379
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7. Bulter C.D., Inman A.G., and Alper H. J. Org. Chem. 65 (2000) 5887
8. +: calcd. 355.1810, found 355.1811.
9. Scheiner P. J. Org. Chem. 32 (1967) 2628
10. Figeys H.P. Tetrahedron Lett. 22 (1981) 637
11. Zuo, G.; Louie, J. Unpublished results.
12. For Pd-catalyzed conversion of aziridines to imines, see:. Wolfe J.P., and Ney J.E. Org. Lett. 5 (2003) 4607
13. NHC catalyze the cyclotrimerization of isocyanates. (See Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679.) Thus, excess isocyanate provided optimal reaction conditions.
14. 2 and NHC alone.
15. +: calcd. 355.1810, found 355.1806.