An efficient process for the bromolactamization of unsaturated acids

Tetrahedron Letters

Volumn 48, Issue 43, 2007, Pages 7567-7570

  Yeung, Ying Yeung ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; LACTAM; LITHIUM; N BENZYLOXYCARBONYL ALPHA LACTAM; N BROMOSUCCINIMIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 34548827964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.113     Document Type: Article

References (10)

1. Yeung Y.-Y., Hong S., and Corey E.J. J. Am. Chem. Soc. 128 (2006) 6310
2. Knapp S., and Levorse A.T. J. Org. Chem. 53 (1988) 4006
3. For some other applications of halolactamization, see:. Boeckman Jr. R.K., and Connell B.T. J. Am. Chem. Soc. 117 (1995) 12368
4. Fujita M., Kitagawa O., Suzuki T., and Taguchi T. J. Org. Chem. 62 (1997) 7330
5. Review on lactam formation:. Robin S., and Rousseau G. Tetrahedron 54 (1998) 13681-13736
6. Martín A., Pérez-Martin I., and Suárez E. Org. Lett. 7 (2005) 2027
7. Love B., and Kormendy M.F. J. Org. Chem. 28 (1963) 3421
8. 4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexane-EtOAc, 5:1) to give the desired Boc-imide 5 (84 mg, 75%) as a colorless solid.
9. 4), filtered, and concentrated and in vacuo. The residue was purified by flash column chromatography (n-hexane-EtOAc, 5:1) to give the desired lactam 13 (72 mg, 94%) as a colorless solid.
10. Shen M., and Li C. J. Org. Chem. 69 (2004) 7906-7909