79828-36-7Relevant academic research and scientific papers
Domino Strategy for the Stereoselective Construction of Angularly Fused Tricyclic Ethers
Subba Reddy,Medaboina, Durgaprasad,Gopal Reddy,Hanuman Reddy,Singarapu, Kiran Kumar,Sridhar, Balasubramanian
, p. 12580 - 12587 (2015)
A stereoselective synthesis of decahydrofuro[3,2-d]isochromene derivatives has been achieved by the condensation of 2-cyclohexenylbutane-1,4-diol with aldehydes in the presence of a stochiometric amount of BF3·OEt2 in dichloromethane at -78 °C. Similarly, the condensation of 2-cyclopentenylbutan-1,4-diol with aldehydes provides the corresponding octahydro-2H-cyclopenta[c]furo[2,3-d]pyran derivatives in good yields with high diastereoselectivity. It is an elegant strategy for the quick construction of tricyclic architectures with four contiguous stereogenic centers in a single step. These tricyclic frameworks are the integral part of numerous natural products.
DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES.
Snider,Rodini,Kirk,Cordova
, p. 555 - 563 (2007/10/02)
Dimethylaluminum chloride, which is a mild Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic and aromatic aldehydes with alkenes containing a disubstituted vinylic carbon. Proton-initiated rearrangements do not occur, since the alcohol-Lewis acid complex formed in the ene reaction reacts rapidly to give methane and a nonacidic aluminum alkoxide. Formaldehyde and excess Me//2AlCl give good yields of ene adducts with all types of alkenes. With 1 equiv of Me//2AlCl, formaldehyde and mono- and 1,2-disubstituted alkenes give gamma -chloro alcohols resulting from cis addition of chlorine and hydroxymethyl groups to the double bond. This work is pertinent to the synthesis of alcohols.
