Hydroxy group-directed homolytic hydrostannylation of alkenols with dibutylchlorostannane

Chemistry Letters

Volumn , Issue 7, 1999, Pages 659-660

  Miura, Katsukiyo ^a   Saito, Hiroshi ^a   Uchinokura, Shingo ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245518     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.659     Document Type: Article

References (17)

1. Review: P. Renaud and M. Gerster, Angew. Chem., Int. Ed. Engl., 37, 2562 (1998).
2. M. Pereyre, J.-P. Quintard, and A. Rahm, "Tin in Organic Synthesis," Butterworths, London (1987).
3. a) W. P. Neumann and R. Sommer, Ann., 675, 10 (1964).
4. b) H. G. Kuivila and R. Sommer, J. Am. Chem. Soc., 89, 5616 (1967).
5. K. Miura, T. Matsuda, T. Hondo, H. Ito, and A. Hosomi, Synlett, 1996, 555; K. Miura, D. Itoh, T. Hondo, H. Saito, H. Ito, and A. Hosomi, Tetrahedron Lett., 37, 8539 (1996).
6. K. Miura, T. Matsuda, T. Hondo, H. Ito, and A. Hosomi, Synlett, 1996, 555; K. Miura, D. Itoh, T. Hondo, H. Saito, H. Ito, and A. Hosomi, Tetrahedron Lett., 37, 8539 (1996).
7. 2ClSnH gives (Z)-vinylstannanes, and the ether oxygen determines the reaction course. T. N. Mitchell and S.-N. Moschref, Chem. Commum., 1998, 1201.
8. 3SnH have been reported; however, the origin of the selectivity is not mentioned, or it is independent of the Lewis acid-base interaction. H. E. Ensley, R. R. Buescher, and K. Lee, J. Org. Chem., 47, 404 (1982); J. C. Anderson and C. A. Roberts, Tetrahedron Lett., 39, 159 (1998).
9. 3SnH have been reported; however, the origin of the selectivity is not mentioned, or it is independent of the Lewis acid-base interaction. H. E. Ensley, R. R. Buescher, and K. Lee, J. Org. Chem., 47, 404 (1982); J. C. Anderson and C. A. Roberts, Tetrahedron Lett., 39, 159 (1998).
10. 2ClSnH has been reported although the directing effect of the hydroxy group is not mentioned in the literature: W. P. Neumann and J. Pedain, Tetrahedron Lett., 1964, 2461. We found that internal alkenes bearing a hydroxy group at the allylic position underwent no hydrostannylation by procedure A or B.
11. K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 109, 2547 (1987).
12. 1H NMR analysis of the crude product. Under the same conditions, 10 mol% of galvinoxyl prevented the reaction completely. This observation suggests that the spontaneous hydrostannylation proceeds via a radical chain mechanism.
13. A. K. Sawyer and H. G. Kuivila, Chem. Ind., 1961, 260.
14. 2ClSnH and its high concentration.
15. 2ClSnH and its high concentration.
16. 2ClSnH in the absence of the coordination of the ether oxygen to the Lewis acidic tin center. See Eq. 4.
17. G. Stork and R. Mook, Jr., J. Am. Chem. Soc., 109, 2829 (1987).