260050-03-1Relevant articles and documents
Allyl alcohols and organocerium reagents, II. - Mechanism and extensibility of the reaction
Bartoli, Giuseppe,Bellucci, M. Cristina,Bosco, Marcella,Dalpozzo, Renato,De Nino, Antonio,Sambri, Letizia,Tagarelli, Antonio
, p. 99 - 104 (2000)
Alkylcerium reagents add to the multiple bonds of allyl and propargyl alcohols in good yields and under mild conditions. The double bond can be reduced with lithium aluminum hydride in the presence of cerium trichloride. The regiochemistry of the attack depends on electronic factors.
Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase
Hutchison, Panee C.,Heightman, Tom D.,Procter, David J.
, p. 790 - 801 (2007/10/03)
A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.