138382-27-1Relevant articles and documents
Conversion of allylic alcohols into allylic nitromethyl compounds via a palladium-catalyzed solvolysis: An enantioselective synthesis of an advanced carbocyclic nucleoside precursor
Deardorff, Donald R.,Savin, Kenneth A.,Justman, Craig J.,Karanjawala, Zarir E.,Sheppeck II, James E.,Hager, David C.,Aydin, Nebil
, p. 3616 - 3622 (1996)
A two-step reaction sequence to homoallylic nitro compounds from allylic alcohols is presented. Ethoxy carbonylation of the alcohols with ethyl chloroformate provides the corresponding allylic ethyl carbonates in high yields. Exposure of these substrates to catalytic palladium(0) in CH3NO2 initiates a reaction sequence, ionization-decarboxylation-nitromethylation, that culminates with the formation of nitroalkenes. The regio- and stereochemical outcomes of the nitromethyl allylation reaction can be explained by the behavior of the transient π-allylpalladium complexes. This methodology serves as a centerpiece for the synthesis of an important carbocyclic nucleoside intermediate.
A flexible synthesis of carbanucleosides and 5′-nor-1′-homo carbanucleosides from a common precursor
Rajappan, Vasathakumar P,Yin, Xueqiang,Schneller, Stewart W
, p. 9889 - 9895 (2007/10/03)
Enzymatic resolution of (±)-1-acetoxy-4-(nitromethyl)-2-cyclopentene (4) provides entry into a facile 10-step route to carbanucleosides and a practical 7-step procedure to 5′-nor-1′-homo carbanucleosides. These routes are illustrated for adenine derivatives but they are adaptable to any heterocyclic base.
