60729-69-3Relevant 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 (2004)
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.
Synthesis of α-Unsubstituted Aldol Adducts Utilizing Enantiomerically Pure β-Keto-δ-Dioxolane Sulfoxides
Blase, Frances Rose,Le, Hung
, p. 4559 - 4562 (2007/10/02)
We report an efficient means to synthesize either enantiomer of α-unsubstituted aldol adduts in high enantiomeric excess through the use of β-keto-δ-dioxolane sulfoxide 4.Through a short sequence of reactions, α-unsubstituted aldol products are obtainable in high yield.
A 5C + 5C Bicycloaromatization Reaction via an Aldol Condensation Cascade: A Regioselective Synthesis of Functionalized Naphthalenes from Acyclic Precursors
Stossel, D.,Chan, T. H.
, p. 4901 - 4908 (2007/10/02)
A regioselective synthesis of naphthalene derivatives 51 was developed by the reaction of 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (2) with the 1,3,5-tris-electrophiles 50 and trimethylsilyl triflate.Three carbon-carbon bonds are formed in this aldol condensation cascade, where the regiochemistry is controlled by the different reactivities at the sites of the acyclic precursors.
