55976-14-2Relevant academic research and scientific papers
Cobalt-catalysed asymmetric hydrovinylation of 1,3-dienes
Timsina, Yam N.,Sharma, Rakesh K.,Rajanbabu
, p. 3994 - 4008 (2015/06/25)
In the presence of bidentate 1,n-bis-diphenylphosphinoalkane-CoCl2 complexes {Cl2Co[P ～ P]} and Me3Al or methylaluminoxane, acyclic (E)-1,3-dienes react with ethylene (1 atmosphere) to give excellent yields of hydrovinylat
Silicon-Mediated Skipped Diene Synthesis. Application to the Melon Fly Pheromone
Wilson, Stephen R.,Zucker, Paul A.
, p. 4682 - 4693 (2007/10/02)
The 1,4-diene unit is a key structural feature of many fatty acid derived natural products including arachidonic acid, several of the leukotrienes, and a variety of insect pheromones.In this paper substituted cyclopropyl>carbinols are demonstrated to cleave redily, upon treatment with acid or upon conversion to the corresponding mesylates, to give mono- and disubstituted 1,4-pentadienes.Stereoselective formation of cis and trans olefins from diastereomeric carbinols has been examined.Control of configuration at the olefin derived from the trimethylsilyl-bearing terminus of the cyclopropane system was found to be only moderate while the olefin derived from the carbinol terminus of the cyclopropane system was produced with high trans stereoselectivity.From these results it is concluded that the cleavage of the cyclopropane ring is neither significantly accelerated by, nor strongly coupled to, cleavage of the carbon-silicon bond.The high stereoselectivity observed for the formation of the trans configuration at the olefin derived from the carbinol terminus has been applied to the synthesis of a constituent of the melon fly pheromone.
Structural Dynamics of Pentadienyl Metal-Compounds Bearing a Terminal Alkyl Substituent: Both 'Stereoselective' and 'Stereodefensive' Synthesis of a Natural Perfume
Bosshardt, Herbert,Schlosser, Manfred
, p. 2393 - 2403 (2007/10/02)
The (2Z,4E)-, (2E,4Z)- and (2E,4E)-isomers of 2,4-decandien-1-ol (5) have been obtained with high and predictable stereochemical homogeneity starting from both (Z)- and (E)-1,4-decadiene.These hydrocarbons were hydroxylated in a reaction sequence consisting of metallation (by means of s-butyllithium or butyllithium/potassium-t-butoxide, giving rise to organometallic intermediates of specific conformations), dimethoxyborylation and oxidation.The different decadienols as well as (2E,4Z)-2,4-undecadien-1-ol were converted into the isovalerates, the ester derived from (2E,4Z)-2,4-decadien-1-ol being a natural flavor component.
