Tethered α-boryl radical cyclizations of haloalkyl boronates

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9183-9187

  Batey, Robert A ^a   Smil, David V ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Boronates; Cyclization; Diols; Radical reactions

Indexed keywords

ALKANEDIOL DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BORONIC ACID DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL BOND; CYCLIZATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033601397     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01970-X     Document Type: Article

References (20)

1. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300.
2. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501.
3. For reviews on silicon-tethered reactions, see: (a) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854.
4. (b) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
5. Guennouni, N.; Lhermitte, F.; Cochard, S.; Carboni, B. Tetrahedron 1995, 51, 6999-7018.
6. (a) Batey, R. A.; Pedram, B.; Yong, K.; Baquer, G. Tetrahedron Lett. 1996, 37, 6847-6850.
7. (b) Takai, K.; Shinomiya, N.; Ohta, M. Synlett 1998, 253-254.
8. Batey, R. A.; Smil, D. V. Angew. Chem., Int. Ed. Engl. 1999, 38, 1798-1800; Angew. Chem. 1999, 111, 1914-1917.
9. Batey, R. A.; Smil, D. V. Angew. Chem., Int. Ed. Engl. 1999, 38, 1798-1800; Angew. Chem. 1999, 111, 1914-1917.
10. Kabalka, G. W.; Slayden, S. W. J. Organomet. Chem. 1977, 125, 273-280.
11. Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632.
12. Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941-6944.
13. Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555.
14. Kuivila, H. G. J. Am. Chem. Soc. 1954, 76, 876-881.
15. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
16. 4), filtered and concentrated in vacuo to a yellow oil. Purification by column chromatography (silica gel, ethyl acetate/hexanes eluent) afforded the desired 1,3-diol.
17. 2OH signal, and only one peak was observed by GC analysis. For both methods of analysis, authentic samples of 6a and 7a were also run for comparison.
18. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996; pp. 38-50.
19. Matsumoto, K.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1992, 33, 7031-7034.
20. Diisopropyl (α-iodopentyl)boronate 14 was prepared via chloromethyllithium based one carbon homologation of diisopropyl butylboronate, followed by halogen exchange to the iodide (see: Matteson, D. S.; Majimdar, D. Organometallics 1983, 11, 1529-1535).