Ester Homologation via α-Bromo α-Keto Dianion Rearrangement

Journal of the American Chemical Society

Volumn 107, Issue 5, 1985, Pages 1429-1430

  Kowalski, Conrad J ^a   Haque, M Seraiul ^a   Fields, Kevin W ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001537249     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00291a063     Document Type: Article

References (12)

1. Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321.
2. It is important that lithium tetramethylpiperidide be used to deprotonate the methylene bromide in this step, to avoid formation of undesired dialkylamide byproducts (corresponding to esters 2) in the final quench.
3. Villieras, J.; Bacquet, C.; Normant, J.-F. Bull. Soc. Chim. Fr. 1975, 1797.
4. Sekine, M.; Nakajima, M.; Kum, A.; Hashizume, A.; Hata, T. Bull. Chem. Soc. Jpn. 1982, 55, 224.
5. Terashima, S.; Tseng, C. C.; Koga, K. Chem. Pharm. Bull. 1979, 27, 747.
6. All new compounds afforded proper combustion analysis as well as IR, NMR, and mass spectra.
7. Gerkin, R. M.; Rickborn, B. J. Am. Chem. Soc. 1967, 89, 5850.
8. Prepared via hydrogenation of the corresponding alkyne over Lindlar catalyst; for a similar prep, see: Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronehi, A. J. Org. Chem. 1981, 46, 5344.
9. Uijttewaal, A. P.; jonkers, F. L.; van der Gen, A. J. Org. Chem. 1979, 44, 3157.
10. Hooz, J.; Layton, R. B. Can. J. Chem. 1972, 50, 105.
11. From chromatographic separation of commercially available material (Aldrich). (13) Nakata, T.; Kuwabara, T.; Tani, Y.; Oishi, T. Tetrahedron Lett. 1982, 23, 1015.
12. Backmann, W. E.; Struve, W. S. Org. React. (N.Y.) 1942, 1, 38.