β-alkoxyacrylate radical cyclization mediated by hypophosphite and triethylborane in ethanol

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7295-7296

  Lee, Eun ^a   Han, Hee Oon ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYLPIPERIDINIUM HYPOPHOSPHITE; ACRYLIC ACID DERIVATIVE; ALCOHOL; BORANE DERIVATIVE; PHOSPHITE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 0037037891     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01751-3     Document Type: Article

References (13)

1. Barton D.H.R., Jang D.O., Jaszberenyi J.C. Tetrahedron Lett. 33:1992;2311-2314.
2. Barton D.H.R., Jang D.O., Jaszberenyi J.C. Tetrahedron Lett. 33:1992;5709-5712.
3. Jang D.O. Tetrahedron Lett. 37:1996;5367-5368.
4. Takamatsu S., Katayama S., Hirose N., Naito M., Izawa K. Tetrahedron Lett. 42:2001;7605-7608.
5. Graham S.R., Murphy J.A., Coates D. Tetrahedron Lett. 40:1999;2415-2416.
6. Graham S.R., Murphy J.A., Kennedy A.R. J. Chem. Soc., Perkin Trans. 1. 1999;3071-3073.
7. Martin C.G., Murphy J.A., Smith C.R. Tetrahedron Lett. 41:2000;1833-1836.
8. McCague R., Pritchard R.G., Stoodley R.J., Williamson D.S. Chem. Commun. 1998;2691-2692.
9. Roy S.C., Guin C., Rana K.K., Maiti G. Tetrahedron. 58:2002;2435-2439.
10. Yorimitsu, H.; Shinokubo, H.; Oshima, K. Chem. Lett. 2000, 104-105. Oshima also reported radical cyclization of the crotyl ether of 2-iodophenol and 2-iodooethanal allylic acetals in ethanol at room temperature in the presence of triethylborane, which were less efficient than in hot ethanol.
11. Kita Y., Nambu H., Ramesh N.G., Anilkumar G., Matsugi M. Org. Lett. 3:2001;1157-1160.
12. Lee E. Renaud P., Sibi M.P., Radicals in Organic Synthesis, Vol. 2: Applications. 2001;303-333 Wiley-VCH, Weinheim.
13. Lee E., Choi S.J., Kim H., Han H.O., Kim Y.K., Min S.J., Son S.H., Lim S.M., Jang W.S. Angew. Chem., Int. Ed. 41:2002;176-178.