An Epoxidation Approach to a Chiral Lactone:  Application of the Shi Epoxidation

An Epoxidation Approach to a Chiral Lactone:  Application of the Shi Epoxidation

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 unsatura...

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Bibliographic Details
Published in:Organic process research & development Vol. 11; no. 1; pp. 44 - 51
Main Authors: Ager, David J, Anderson, Ken, Oblinger, Eric, Shi, Yian, VanderRoest, James
Format: Journal Article
Language:English
Published: American Chemical Society 01-01-2007
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op060140e