916525-75-2Relevant articles and documents
Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses
Broeker, Joachim,Knollmueller, Max,Gaertner, Peter
scheme or table, p. 273 - 287 (2009/09/05)
The applicability of five aryl substituted m-hydrobenzoin ethers already tested in the L-Selectride mediated stereoselective reduction of phenylglyoxylates as open chain chiral auxiliaries was further investigated via the α-alkylation of propionates, the addition of n-BuZnCl to phenylglyoxylates and the Diels-Alder reaction of acrylates with cyclopentadiene as model reactions. As up to 90% de could be achieved in the solution phase, two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliaries in the same type of reactions.