An epoxidation approach to a chiral lactone: Application of the Shi epoxidation

DJ Ager, K Anderson, E Oblinger, Y Shi…

Index: Ager, David J.; Anderson, Ken; Oblinger, Eric; Shi, Yian; Vanderroest, James Organic Process Research and Development, 2007 , vol. 11, # 1 p. 44 - 51

Full Text: HTML

Citation Number: 31

Abstract

The large-scale epoxidation of the alkene 7 with the organocatalyst, Epoxone (10), and Oxone as the oxidant is described. This is the first large-scale application of the Shi epoxidation methodology. The large-scale preparation of the catalyst 10 is also described. The potassium salt of the unsaturated acid precursor 7 was prepared by a Suzuki coupling from 3-fluorobenzyl chloride and the vinylborane 8 derived from 4-pentynoic acid.

Related Articles:

Hydroboration. XIII. The hydroboration of dienes with disiamylborane. A convenient procedure for the conversion of selected dienes into unsaturated alcohols

[Zweifel,G. et al. Journal of the American Chemical Society, 1962 , vol. 84, p. 190 - 195]

Addition compounds of alkali-metal hydrides. 25. Facile reaction of borinic esters with lithium monoethoxyaluminohydride to form lithium dialkylborohydrides

[Singaram, Bakthan; Cole, Thomas E.; Brown, Herbert C. Organometallics, 1984 , vol. 3, p. 1520 - 1523]

More Articles...