721916-83-2Relevant articles and documents
A β,β′-ketoaminoester as a valuable tool for the asymmetric construction of substituted homopipecolic esters: Application to a formal synthesis of (+)-Calvine
Rougnon-Glasson, Sophie,Tratrat, Christophe,Canet, Jean-Louis,Chalard, Pierre,Troin, Yves
, p. 1561 - 1567 (2007/10/03)
A highly diastereoselective 1,4-addition involving Davies' lithium amide is employed as the key reaction to prepare, in five steps from ethyl acetoacetate, an enantiomerically pure keto protected β,β′- ketoaminoester. This latter was reacted with aldehydes in an intramolecular Mannich process and furnished a direct and stereoselective access to substituted homopipecolates. The validity of this approach was achieved through a new formal asymmetric synthesis of alkaloid (+)-Calvine.
