The synergy of a solution-phase preparation of scaffolds with a solid-phase combinatorial synthesis let to develop an efficient route to a small library of chiral, highly functionalized tetrahydroisoquinolines. Both loading on the Merrifield resin and the key acid-catalyzed Pictet-Spengler condensation were efficiently promoted by microwave irradiation. The library was designed such that up to five points of diversity would be potentially introduced, making the strategy in principle suitable for generation of a large number of compounds.
Microwave-Assisted, Solid-Phase Synthesis of a Chiral 1,2,3,4-Tetrahydroquinoline Library / G. Lesma, B. Danieli, F. Lodroni, D. Passarella, A. Sacchetti, A. Silvani.. - In: COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING. - ISSN 1386-2073. - 9:9(2006), pp. 691-701.
Microwave-Assisted, Solid-Phase Synthesis of a Chiral 1,2,3,4-Tetrahydroquinoline Library
G. LesmaPrimo
;B. DanieliSecondo
;D. Passarella;A. SacchettiPenultimo
;A. Silvani.Ultimo
2006
Abstract
The synergy of a solution-phase preparation of scaffolds with a solid-phase combinatorial synthesis let to develop an efficient route to a small library of chiral, highly functionalized tetrahydroisoquinolines. Both loading on the Merrifield resin and the key acid-catalyzed Pictet-Spengler condensation were efficiently promoted by microwave irradiation. The library was designed such that up to five points of diversity would be potentially introduced, making the strategy in principle suitable for generation of a large number of compounds.Pubblicazioni consigliate
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