Alkylation epoxide rearrangement. Application to stereoselective synthesis of chiral pheromone epoxides.

✍ Scribed by Thomas W. Bell; James A. Ciaccio

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 247 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82468-5

✦ Synopsis

An approach is described for the stereospectfb conversbn of threo and erythro 1 ,P-epoxy-3-alkanol tosyiates to cis and trans internal epoxktes. mspectively. Ths method ts illustrated by the synthesis of chiral epoxkfes, tnckxiing insect pheromones. Synthetic chemists face a major challenge in the preparation of chiral compounds having very high optical purity. The need for pure enantiomers fs partiwtarty apparent in the field of pheromone chembtry. since insect chemoreceptbn can be highly stereosebctive.l,2 Cptiily acttve 2,3-epoxy-l-akamls are common intermediates in the preparatbn of insect pheromones 3 and may he obtained hy asymmetric epoxkfatiin of allylb abohols or through the Payne rearrangement4 of readily available 1,2-16) For a synthesis of (+)diiparfure from a 1 ,bepoxy-3-akanol in which the stereochemistry of the epoxide ring iS the same as expected in the Payne rearrangement, refer to: