New Fe(III)-mediated radical cascade reactions of cyclopropyl silyl ethers

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1107-1109

  Booker Milburn, Kevin I ^a   Jones, J Leighton ^a   Sibley, Graham E M ^a   Cox, Richard ^b   Meadows, Jim ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IRON DERIVATIVE; KETONE DERIVATIVE; RADICAL; SILANE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; RING OPENING; STEREOCHEMISTRY;

EID: 0141853769     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341703     Document Type: Article

References (9)

1. Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
2. Booker-Milburn, K. I.; Barker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321.
3. Independent studies by Narasaka and co-workers showed that Mn(III) could be used to effect similar transformations with cyclopropanols: Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Ikeno, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1999, 72, 85.
4. Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
5. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974.
6. Jenkins, H. Unpublished results.
7. See Supporting Information.
8. (a) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 2674.
9. (b) For an annulation sequence involving abstraction/cyclization reactions of cyclopropylamines, see: Ha, J. D.; Lee, J.; Blackstock, S. C.; Cha, J. K. J. Org. Chem. 1998, 63, 8510.