Catalytic, asymmetric dimerization of methylketene

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8006-8007

  Calter, Michael A ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001547021     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961721c     Document Type: Article

References (14)

1. Wynberg, H. Top. Stereochem. 1986, 16, 87.
2. Sauer, J. C. J. Am. Chem. Soc. 1947, 69, 2444.
3. Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157.
4. (a) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166.
5. (b) Wynberg, H.; Staring, E. G. J. J. Org. Chem. 1985, 50, 1977.
6. McCarney, C. C.; Ward, R. S. J. Chem. Soc., Perkin Trans. 1 1975, 1600.
7. The enantiomeric excess of 3 was assayed by conversion to the corresponding Mosher ester followed by GC analysis. The configuration of the major enantiomer produced was established by comparison of the rotation of this compound to the rotation of 3 derived from methyl (S)-(+)-3-hydroxy-2-methylpropionate (see ref 7).
8. Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013.
9. Masters, A. P.; Sorensen, T. S.; Ziegler, T. J. Org. Chem. 1986, 51, 3559.
10. These results are similar to Wynberg's results with acylated catalysts in the addition of ketene to chloral (ref 4a).
11. There are numerous examples of nucleophiles adding to aldoketenes opposite the larger substituent. For example, see: Dondoni, A.; Fantin, G.; Fogagnolo, M.; Mastellari, A.; Medici, A.; Pedrini, P. J. Org. Chem. 1984, 49, 3478.
12. Dijkstra, G. D. H.; Kellog, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
13. (a) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romera, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
14. (b) Paterson, I,; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925.