A novel asymmetric vinylogous tin-pummerer rearrangement

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1757-1760

  García Ruano, José Luis ^a   Aleman, José ^a   Padwa, Albert ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BENZYL DERIVATIVE; CARBOXYLIC ACID; CHLORIDE; ION; SOLVENT; TIN; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONJUGATION; ENANTIOSELECTIVITY; PUMMERER REACTION; STEREOCHEMISTRY; TEMPERATURE;

EID: 2942600190     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495725     Document Type: Article

References (17)

1. (a) Pummerer, R. Chem Ber. 1909, 42, 2282.
2. (b) DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A., Ed.; Wiley: 1991; Chapter 3, pp 157-184.
3. (c) Grierson, D. S.; Husson, H. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947.
4. (d) Kennedy, M.; McKervey, M. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 7, pp 193-217.
5. (a) Padwa, A.; Gunn, D. E.; Osterhout, H. M. Synthesis 1997, 1353.
6. (b) Padwa, A.; Pure Appl. Chem. 2003, 75, 47.
7. Kuethe, T.; Padwa, A. J. Org. Chem. 1998, 63, 4256.
8. Block, E.; Aslam, M. Tetrahedron 1988, 44, 284 and references therein.
9. (a) Beddoes, R. L.; Macleod, D.; Moorcroft, D.; Queayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 417.
10. (b) Pohmakotr, M.; Sithikanchanakul, S. Tetrahedron Lett. 1989, 30, 6773.
11. For reaction with carbonyl groups, see: García Ruano, J. L.; Aranda, M.; Carreño, M. C.; Toledo, M. A. Angew. Chem., Int. Ed. 2000, 39, 2736.
12. For reaction with imines, see: (a) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677. (b) Garcia Ruano, J. L.; Alemán J. Org. Lett. 2003, 5, 4513.
13. For reaction with imines, see: (a) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677. (b) Garcia Ruano, J. L.; Alemán J. Org. Lett. 2003, 5, 4513.
14. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129.
15. Shie, J. Y.; Lin, Y. C.; Wang, Y. J. Organomet. Chem. 1989, 3, 383 and references therein.
16. Reactions involving the stereoselective formation of cyclobutanes from precursors of 1,4-zwitterionic species have been widely reported (see: Taylor, R. E.; Engelhardt, C. F.; Schmitt, M. J. Tetrahedron 2003, 59, 5623 and references therein). They are electronically similar to those involving the direct transformation of 19 into 22 in just one step.
17. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.