6414-24-0Relevant academic research and scientific papers
Intramolecular Diels-Alder reaction of functionalized trienes: Synthesis of medium-ring lactones
Deagostino, Annamaria,Maddaluno, Jacques,Mella, Mariella,Prandi, Cristina,Venturello, Paolo
, p. 881 - 888 (1998)
A simple preparative procedure has been developed for trienic systems, starting from cyclic α,β-unsaturated acetals derived from crotonaldehyde and (E)-pent-2-enal. The reaction is initiated by a regioselective metallation at the γ site of the unsaturated
New 2,4,6-substituted 1,3-dioxanes: Synthesis, stereochemistry and thermodynamic data determinations by cis-trans isomers equilibrium
Balog, Mirela,Ramondenc, Yvan,Oprean, Ioan,Grosu, Ion,Ple, Gerard
, p. 389 - 394 (2007/10/03)
The thermodynamic data (A-values) for some substituents located at position 2 of the 1,3-dioxane ring are calculated from the ratio (measured by GC-MS and NMR) of cis and trans isomers of some 2,4,6-substituted-1,3-dioxanes obtained by the condensation reaction of meso 2,4-pentanediol with several aldehydes and ketones. The stereochemistry of these compounds is deduced from high-field NMR experiments.
ASYMMETRIC SIMMONS-SMITH REACTIONS USING HOMOCHIRAL PROTECTING GROUPS
Mori, Atsunori,Arai, Isao,Yamamoto, Hisashi,Nakai, Hisao,Arai, Yoshinobu
, p. 6447 - 6458 (2007/10/02)
Asymmetric Simmons-Smith reactions of α,β-unsaturated acetals derived from chiral dialkyl tartrate or (2R,4R)-2,4-pentanediol are described.Treatment of the acetal with diethylzinc and methylene iodide gives a cyclopropane with high diastereoselectivity.The acetal group is readily transformed to the aldehyde or the ester group.In addition, the method is successfully applied to the enantioselective synthesis of 5,6-methanoleukotriene A4, a stable and selective inhibitor of leukotriene biosynthesis.
DIASTEREOSELECTIVE CONJUGATE ADDITION TO CHIRAL α,β ETHYLENIC ACETALS
Mangeney, P.,Alexakis, A.,Normant, J. F.
, p. 3143 - 3146 (2007/10/02)
The phenyl copper reagent associated with Lewis acid (BF3) reacts regio (SN2') and stereoselectively with chiral α,β ethylenic acetals.
