The team is engaged in the synthesis of several targets of general synthetic interest by applying in-house developed methodologies as key steps. The research of the team in this area, classified by date, is exemplified here below by a concise description of the publications spanning the period 2007-2012.
Stereoselective Synthesis of syn-Β-Amino Propargylic Ethers : Application to the Asymmetric Syntheses of (+)-Β-Conhydrine and (–)-Balanol. The stereoselective synthesis of syn-Β-amino propargylic ethers by the addition of racemic lithio 3-(methoxymethoxy) allenylcuprates, and more particularly (cyano) and (mesityl)cuprates, to enantiopure chiral N-tert-butylsulfinylimines is reported. The scope and limitations of the reaction is studied. The usefulness of the methodology for the synthesis of compounds having a syn-1,2-amino alcohol unit is shown through the development of the asymmetric syntheses of (+)-Β-conhydrine and of an advanced intermediate of (–)-balanol. (+)-Β-Conhydrine was obtained in 6 steps and 33% yields from 5-chloropentanal, while the advanced intermediate of (–)-balanol was obtained in 7 steps and 35% yield from a know acetal.