Juliá–Colonna stereoselective epoxidation of some α, β-unsaturated enones possessing a stereogenic centre at the γ-position: synthesis of a protected galactonic …
PC Ray, SM Roberts
Index: Ray, Peter C.; Roberts, Stanley M. Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 2 p. 149 - 153
Full Text: HTML
Citation Number: 20
Abstract
The oxidation of enones 6–8 using peroxide or percarbonate and polyleucines as catalysts gave the corresponding diastereomers 9–12 in high yield. The compound 9 was converted into the galactonic acid derivative 16 in five steps and in an overall yield of nearly 60%. Polyleucines are shown to be catalysts powerful enough to overturn the intrinsic stereocontrol in the chosen substrates. p
Related Articles:
Reactions of Hydrogen Peroxide. V. 1 Alkaline Epoxidation of Acrolein and Methacrolein
[Payne Journal of the American Chemical Society, 1959 , vol. 81, p. 4901,4904]
[Golding, Bernard T.; Slaich, Pritpal K.; Kennedy, Gordon; Bleasdale, Christine; Watson, William P. Chemical Research in Toxicology, 1996 , vol. 9, # 1 p. 147 - 157]
[Machado, Sonia Salgueiro; Wandel, Ute; Jongejan, Jaap A.; Straathof, Adrie J. J.; Duine, Johannis A. Bioscience, Biotechnology and Biochemistry, 1999 , vol. 63, # 1 p. 10 - 20]