Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 14 - Ethers, Epoxides, and Thioethers - Problems: Problem 14-20 b

Answer

Sharpless epoxidation give just one nearly pure enantiomer of the product because of the chiralty of the diethyl tartrate.

Work Step by Step

When the chiral diethyl L-tartrate, forms a complex with titanium(IV) isopropoxide, the complex is also chiral. The alkene reaction between alkene and tert-butyl hydroperoxide occurs on one face of the alkene causing the formation of one epoxide stereoisomer. Without the chiral chiral diethyl L-tartrate, there is a formation of racemic products.
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