The BF3 and B(C6F5)3-catalyzed 1,3-isomerization of allylic stannanes

Journal of Organometallic Chemistry

Volumn 624, Issue 1-2, 2001, Pages 294-299

  Marshall, James A ^a   Gill, Kevin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

1,3 Isomerization; Allylic stannanes; Chiral stannanes; Tin boron metathesis; Tris (Pentafluorophenyl)borane

Indexed keywords

EID: 0001669808     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00642-8     Document Type: Article

References (12)

1. Review: Y. Yamamoto, N. Shida, in: Advances in Detailed Reaction Mechanisms, vol. 3, JA1 Press, 1994, pp. 1-44.
2. A. Boaretto, D. Marton, G. Tagliavini, F.J. Ganis, J. Organomet. Chem. 321 (1987) 199.
3. S.E. Denmark, T. Wilson, T.M. Willson, J. Am. Chem. Soc. 110 (1988) 984.
4. S.E. Denmark, E.J. Weber, T.M. Wilson, T.M. Willson, Tetrahedron 45 (1989) 1053.
5. J.A. Marshall, G.S. Welmaker, B.W. Gung, J. Am. Chem. Soc. 113 (1991) 647.
6. J.M. Blackwell, W.E. Piers, M. Parvez, Org. Lett. 2 (2000) 695.
7. A.D. Horton, J. de With, Organometallics 16 (1997) 5424.
8. 4 in benzene is 263 ppm corresponding to a calculated 33% cation character. We thank a reviewer for pointing out that the positive character of the Sn atom in complex 12 may be diminished by coordination with the OMOM grouping.
9. K. Maruoka, T. Ooi, Chem. Eur. J. 5 (1999) 829.
10. 1H-NMR analysis of the Mosher O-methylmandelic esters. The relative stereochemistry was assigned by analogy and by the characteristic chemical shifts of the OH proton of the syn (3.03 and 3.10 ppm) and anti (2.77 ppm) adducts. J.A. Marshall, A.W. Garofalo, J. Org. Chem. 61 (1996) 8732.
11. J.A. Marshall, Chem. Rev. 96 (1996) 31.
12. H. Yamataka, K. Nishikawa, T. Hanafusa, Chem. Lett. (1990) 1711.