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US 11,155,505 B2Granted
Synthesis of pheromones and related materials via olefin metathesis
AssigneeProvivi, Inc.
InventorsKeith M. Wampler, Vu Bui, David Rozzell, Pedro Coelho, Arthur Floruti, Levente Ondi, Hasan Mehdi, Gabor Eros
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Abstract
Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
Claims17
A method for synthesizing a compound according to Formula III, the method comprising:
- a) contacting an alkyl ester of 9-decenoate with a ruthenium isomerization catalyst or an iridium isomerization catalyst to form an alkyl ester of 8-decenoate;
- and
- b) contacting an olefin according to Formula I
- with the alkyl ester of dec-8-enoate
- in the presence of a metathesis catalyst to form the compound according to Formula III:
- wherein the metathesis catalyst is a molybdenum catalyst, a tungsten catalyst, or a ruthenium catalyst;
- and
- wherein:
- R1 is selected from the group consisting of hydrogen and C1-18 alkyl;
- R2 is C1-18 alkyl;
- R4 is —C(O)OR4b;
- R4b is C1-8 alkyl;
- and
- subscript y is 6.
11 more elements
Dependencies are inferred from the claim text.