Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

Tetrahedron Letters

Volumn 48, Issue 48, 2007, Pages 8550-8553

  Clayden, Jonathan ^a   Hebditch, Katherine R ^a   Read, Benjamin ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BICYCLIC HYDROXYSILANE; KAINIC ACID DERIVATIVE; KAINOID DERIVATIVE; PYRROLIDINE DERIVATIVE; SILANE DERIVATIVE; TIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; FRAGMENTATION REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 35548962680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.150     Document Type: Article

References (20)

1. Clayden J. In: Harmata M. (Ed). Strategies and Tactics in Organic Synthesis (2004), Academic Press 72-96
2. Clayden J., Read B., and Hebditch K.R. Tetrahedron 61 (2005) 5713
3. Clayden J., Knowles F.E., and Baldwin I.R. J. Am. Chem. Soc. 127 (2005) 2412
4. Clayden J., and Tchabanenko K. Chem. Commun. (2000) 317
5. Clayden J., Menet C.J., and Tchabanenko K. Tetrahedron 58 (2002) 4727
6. Clayden J., Knowles F.E., and Menet C.J. Tetrahedron Lett. 44 (2003) 3397
7. Ahmed A., Bragg R.A., Clayden J., and Tchabanenko K. Tetrahedron Lett. 42 (2001) 3407
8. Parsons A.F. Tetrahedron 52 (1996) 4149
9. Posner G.H., Webb K.S., Asirvatham E., Jew S.-S., and Degl'Innocenti A. J. Am. Chem. Soc. 110 (1988) 4754
10. Posner G.H., Wang Q., Halford B.A., Elias J.S., and Maxwell J.P. Tetrahedron Lett. 41 (2000) 9655
11. Nakatani K., and Isoe S. Tetrahedron Lett. 25 (1984) 5335
12. Baldwin J.E., Adlington R.M., and Robertson J. Chem. Commun. (1988) 1404
13. Hatcher M.A., Borstnik K., and Posner G.H. Tetrahedron Lett. 44 (2003) 5407
14. Krow G.R. Org. React. 43 (1993) 251
15. Clayden J., Menet C.J., and Mansfield D.J. Org. Lett. 2 (2000) 4229
16. Posner G.H., and Asirvatham E. Tetrahedron Lett. 27 (1986) 663
17. Crump R.A.N.C., Fleming I., and Urch C.J. J. Chem. Soc., Perkin Trans. 1 (1994) 701
18. The stereoselectivity (exo face attack) of this addition was deduced from the X-ray crystal structures of later derivatives.
19. Goldsmith C.R., Jonas R.T., and Stack T.D.P. J. Am. Chem. Soc. 124 (2002) 83
20. X-ray crystallographic data has been deposited with the Cambridge Crystallographic Data Centre: Deposition numbers: 9a 658992; 21a 658993; 21c 658994.