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

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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.