14959-86-5Relevant articles and documents
SILICON IN ORGANIC SYNTHESIS. STREREOSELECTIVE SYNTHESIS OF SOME INSECT SEX PHEROMONES
Chan, T. H.,Koumaglo, K.
, p. 109 - 120 (1985)
Trialkylsilallyl anion is alkylated by alkyl halides to give regio- and strereo-selectively the γ-product with trans-strereochemistry at double bond.The trans-vinylsilanes are transformed strereoselectively to Z-vinyl iodides.Coupling of the vinyl idiodes with organometallic reagents gives Z-alkenes.This approach has been applied to the synthesis of several insect sex pheromones.
Leznoff,Fyles
, p. 251 (1976)
Vinylic Organoboranes. 3. Pheromones via Organoboranes. 1. Stereospecific Synthesis of Straight-Chain Z-Monoolefinic Insect Pheromones via Lithium (1-Alkynyl)trialkylborates
Brown, Herbert C.,Wang, Kung K.
, p. 4514 - 4517 (1986)
Various insect pheromones with straight-chain Z-monoolefinic structures have been prepared from lithium (1-alkynyl)trialkylborates.Treatment of lithium (1-alkynyl)trialkylborates, readily prepared from lithium acetylides and trialkylboranes, with iodine under mild conditions produces the corresponding alkynes in essentially quantitative yield.Monohydroboration of the resultant alkyne with 9-borabicyclononane yields the corresponding (Z)-olefin after protonolysis.The combination of these two reaction sequences provides a general route for the synthesis of (Z)-olefins.The position of the double bond and the carbon-chain length are easily controlled by properly choosing the initial reactants.The incorporation of functional groups is also easily achieved because of the mild reaction conditions and the tolerance of hydroboration to many functional groups.High yield and purity of the products are obtained.
New synthesis of (Z)-5- and (Z)-7-monoene components of insect sex pheromones of the Lepidoptera order
Bykov,Butenko,Egupova,Finkelshtein
, p. 1301 - 1304 (2000)
A new procedure was developed for the synthesis of (Z)-5- and (Z)-7-monoene components of sex pheromones of Lepidoptera insects based on cometathesis of readily accessible cycloocta-1,5-diene and ethylene.
Pheromone Synthesis via Organoboranes: A Stereospecific Synthesis of (Z)-7-Alken-1-ols
Basavaiah, D.,Brown, Herbert C.
, p. 1792 - 1793 (1982)
Traetment of trans-1-alkenylborepanes, obtained via monohydroboration of 1-alkynes with borepane, with iodine in the presence of a base results in the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, producing intermediates containing the eight-membered borocane moiety, which undergoes a rapid deiodoboronation to afford the (Z)-7-alkenyl-1-boronate esters.These boronate esters on oxidation produce (Z)-7-alken-1-ols, providing a general, one-pot, and stereospecific synthesis of (Z)-7-alken-1-ols.
Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**
Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry
supporting information, p. 19685 - 19690 (2021/08/06)
The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.
PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
-
, (2017/06/12)
In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.
