A β, β′-ketoaminoester as a valuable tool for the asymmetric construction of substituted homopipecolic esters: application to a formal synthesis of (+)-Calvine
S Rougnon-Glasson, C Tratrat, JL Canet… - Tetrahedron …, 2004 - Elsevier
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.
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.
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