Biomedical subjects
Publications and source records attributed to Gianna Reginato.
Aziridinyl ethers are selectively and easily converted to either amino vinyl ethers or alkoxy allylamines by treatment with mixed metal bases (superbases).
Solid-phase organic synthesis (SPOS) is the most important method for the production of combinatorial libraries and with the development of high-throughput screening, libraries are widespread in pharmaceutical and agricultural chemistry. Amongst all the synthetic transformations successfully applied to solid phase, the use of organometallic reagents for the formation of a new carbon-carbon bond has been scarcely pursued. In this overview we collected the most recent examples of the use of organometallic reagents of Li, Mg, Cu, Zn, Si and B for C-C bond formation. The use of organometallic reagents in Pd-catalysed cross-coupling reactions was not reviewed. Highly basic organometallics as organo-lithium and -magnesium reagents have been more largely employed than cuprates and zincates, suggesting that several kinds of resins can withstand relatively strong reaction conditions.
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The base-promoted isomerization of benzyl oxiranyl ethers was investigated. In particular it was shown that the reaction may proceed toward two main regioisomeric products: a benzyl vinyl ether or a 2-aryl-3-(hydroxyalkyl)oxetane, depending on subtle variations in the substitution on the phenyl ring. Disubstituted oxetanes were obtained in a stereoselective manner, thus providing a good entry to this class of synthetically useful compounds.
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One of the unresolved problems of solid-phase organic synthesis (SPOS) is the availability of general and rapid methods to monitor the transformation of functional groups present in molecules supported on insoluble supports. Color tests, far from providing the ultimate solution, may help in detection (and sometimes in quantification) of different functional groups. In this short review, we have collected most of the methods available and applied in SPOS with an Experimental Section that describes the procedure we have successfully applied to bead analyses in our laboratories.