64275-34-9Relevant articles and documents
Selective formation of non-conjugated olefins by samarium(II)-mediated elimination/isomerization of allylic benzoates
Schaefer, Sara L.,Roberts, Connor L.,Volz, Erasmus O.,Grasso, Monika R.,O'Neil, Gregory W.
, p. 6125 - 6128 (2013/10/22)
Aromatic allylic benzoates can be selectively transformed to the corresponding benzoate eliminated olefin by the action of samarium diiodide. Depending on the substrate and the elimination conditions, high selectivity for the non-conjugated alkene product
Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents
Selim, Khalid B.,Yamada, Ken-Ichi,Tomioka, Kiyoshi
supporting information; experimental part, p. 5140 - 5142 (2009/03/11)
Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(i) complexes. The Royal Society of Chemistry.
Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents
Mechelke, Mark F.,Wiemer, David F.
, p. 4821 - 4829 (2007/10/03)
The synthesis of a family of farnesol analogues, incorporating aromatic rings, has been achieved in high yields through the development of a regioselective coupling of allylic tetrahydropyranyl ethers with organometallic reagents. The allylic THP group is displaced readily by Grignard reagents in the presence of Cu(I) halides but is stable in the absence of added copper. Thus, an allylic THP group can fulfill its traditional role as a protecting group or serve as a leaving group depending on reaction conditions. An improved synthesis of (2E,6E)-10,11-dihydrofarnesol also has been accomplished using this methodology, and some preliminary studies on the reactivity and regioselectivity of THP ether displacements were conducted. The farnesol analogues reported herein may be useful probes of the importance of nonbonding interactions in enzymatic recognition of the farnesyl chain and allow development of more potent competitive inhibitors of enzymes such as farnesyl protein transferase.