Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the lodination of allylically oxygenated α-triphenylstannylalkenes

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5377-5380

  Dimopoulos, Paschalis ^a   George, Jonathan ^a   Tocher, Derek A ^a   Manaviazar, Soraya ^a   Hale, Karl J ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28844467489     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051937d     Document Type: Article

References (16)

1. For part 1, see: (a) Dimopoulos, P.; Athlan, A.; George, J. Manaviazar, S.; Walters, M.; Lazarides, L.; Aliev, A. E.; Hale, K. J. Org. Lett. 2005, 7, 5369.
2. For part 2, see: (b) Dimopoulos, P.; Athlan, A.; Manaviazar, S.; Hale, K. J. Org. Lett. 2005, 7, 5373.
3. Padwa, A.; Rashatasakhon, P.; Daut Ozdemir, A.; Willis, J. J. Org. Chem. 2005, 70, 519.
4. (a) For recent synthetic work and references on the pumiliotoxins see: Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6950.
5. (b) See also: Franklin, A.; Overman, L. E. Chem Rev. 1996, 96, 505.
6. For our asymmetric total synthesis of the antitumor antibiotic A83586C, see: Hale, K. J.; Cai, J. Chem. Commun. 1997, 2913.
7. Stipiamide total synthesis: Andrus, M. B.; Lepore, S. D.; Turner, T. M., J. Am. Chem. Soc. 1997, 119, 12159.
8. Halichomycin synthetic studies: Hale, K. J.; Dimopoulos, P.; Cheung, M. L. F.; Steed, J. W.; Levett, P. Org. Lett. 2002, 4, 897.
9. Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343.
10. Taniguchi, M.; Nozaki, K.; Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1992, 65, 349.
11. Marco-Contelles, J.; Mainetti, E.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2003, 1759.
12. Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541.
13. 2O at rt. For more details, see: Han, X.; Hartmann, G. A.; Brazzale, A.; Gaston, R. D. Tetrahedron Lett. 2001, 42, 5837.
14. 3Sn radicals due to magnified steric hindrance around the radical center; again, this should favor the α-mode of addition.
15. Lalitha, S.; Chandrasekhar, J. Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 259.
16. 1, 3 strain being present within 26.