Please use this identifier to cite or link to this item: http://hdl.handle.net/10637/8989

Microwave-mediated sulfonium ylide cyclopropanation: stereoselective synthesis of cyclopropa[c]pentalenes.

Title: Microwave-mediated sulfonium ylide cyclopropanation: stereoselective synthesis of cyclopropa[c]pentalenes.
Authors : López Rodríguez, Alberto
Pérez Castells, Javier
Domínguez Martín, Gema
Keywords: Pentaleno
Abstract: Stereoselective sulfonium ylide cyclopropanation is a useful transformation due to the presence of this moiety in numerous bioactive compounds. The procedures described to date involve long reaction times and variable stereoselectivity outcomes. We show here that performing these reactions under MW mediation gives good yields and selectivity after short reaction periods. The methodology is applied to different substrates including sterically hindered cyclopentenones, open chain unsaturated esters and pentalenones (Pauson-Khand products). From these latter substrates, highly connected cyclopropa[c]pentalenes were synthesized in good yields, including a precursor of natural product pentalenene.

La ciclopropanación esteloselectiva de iluro de sulfonio es una transformación útil debido a la presencia de este resto en numerosos compuestos bioactivos. Los procedimientos descritos hasta la fecha implican largos tiempos de reacción y resultados variables de estereoselectividad. Mostramos aquí que la realización de estas reacciones bajo mediación de MW da buenos rendimientos y selectividad después de cortos períodos de reacción.
Description: En: ChemistrySelect. e-ISSN 2365-6549. n. 2 (2017), p. 2565-2568
URI: http://hdl.handle.net/10637/8989
Rights : http://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
Issue Date: 9-Mar-2017
Center : Universidad San Pablo-CEU
Appears in Collections:Facultad de Farmacia





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