Reactivity of allenoates toward aziridines: [3+2] and formal [3+2] cycloadditions

Tetrahedron Letters

Volumn 50, Issue 45, 2009, Pages 6180-6182

  Ribeiro Laia, Fernanda M ^a   Pinho e Melo, Teresa M V D ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

3+2 cycloaddition; Allenes; Aziridines; Formal 3+2 cycloaddition; Microwave; Pyrroles; Pyrrolidines

Indexed keywords

1 BENZYL 2 BENZOYL 3 PHENYLAZIRIDINE; AZIRIDINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY;

EID: 70349197598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.088     Document Type: Article

References (20)

1. Pinho e Melo T.M.V.D. Curr. Org. Chem. 13 (2009) 1406-1431
2. In: Krause N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry (2004), WILEY-VCH GmbH & Co. KgaA, Weinheim
3. Ma S. Chem. Rev. 105 (2005) 2829-2871
4. Ma S. Aldrichimica Acta 40 (2007) 91-102
5. Hassan H.H.A.M. Curr. Org. Chem. 4 (2007) 413-439
6. Aziridine 1 (mp 105-107 °C; lit. 108 °C) and aziridine 9 (mp 107.5-109 °C; lit. 107 °C) were prepared as described in. Cromwell N.H., Badson R.D., and Harris C.E. J. Am. Chem. Soc. 65 (1943) 312-315
7. Crystallography data of aziridine 1 will be disclosed in due time.
8. Buta-2,3-dienoates were prepared via Wittig reaction of benzyl(triphenylphosphoranylidene)acetate with ketene following the general procedure described in. Pinho e Melo T.M.V.D., Cardoso A.L., Rocha Gonsalves A.M.dA., Costa Pessoa J., Paixão J.A., and Beja A.M. Eur. J. Org. Chem. (2004) 4830
9. Lambert T.H., and MacMillan D.C.W. J. Am. Chem. Soc. 124 (2002) 13646-13647
10. +], 488.21810).
11. Lopes S.M.M., Beja A.M., Silva M.R., Paixão J.A., Palacios F., and Pinho e Melo T.M.V.D. Synthesis (2009) 2403-2407
12. Aziridine 7 (mp 100-102 °C; lit. 101-102 °C) was prepared as described in. Southwick P.L., and Christman D.R. J. Am. Chem. Soc. 74 (1952) 1886-1891
13. +], 374.20753).
14. Kluger R. Pure Appl. Chem. 69 (1997) 1957-1967
15. Amal Raj A., and Raghunathan R. Tetrahedron 59 (2003) 2907-2911
16. Boruah A., Baruah B., Prajapati D., Sandhu J.S., and Ghosh A. Tetrahedron Lett. 37 (1996) 4203-4204
17. Padwa A., and Hamilton L. Tetrahedron Lett. 48 (1965) 4363-4367
18. Gaebert C., and Mattay J. Tetrahedron 53 (1997) 14297-14316
19. Dalili S., and Yudin A.K. Org. Lett. 7 (2005) 1161-1164
20. Zhu W., Cai G., and Ma D. Org. Lett. 7 (2005) 5545-5548