Continuous-flow organocatalyzed Diels-Alder reactions have been performed with excellent enantioselectivity for the first time in a chiral "homemade" HPLC column, packed with silica on which a MacMillan catalyst has been supported by a straightforward immobilization procedure. The versatility of the system was also proven by running with the same column continuous-flow stereoselective reactions with three different substrates, showing that the catalytic reactor may efficiently work in continuo for more than 150 h; the regeneration of the HPLC column was also demonstrated, allowing to further extend the activity of the reactor to more than 300 operating hours.

Continuous-flow stereoselective organocatalyzed Diels-Alder reactions in a chiral catalytic "homemade" HPLC column / V. Chiroli, M. Benaglia, F. Cozzi, A. Puglisi, R. Annunziata, G. Celentano. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 15:14(2013), pp. 3590-3593.

Continuous-flow stereoselective organocatalyzed Diels-Alder reactions in a chiral catalytic "homemade" HPLC column

V. Chiroli;M. Benaglia;F. Cozzi;A. Puglisi;R. Annunziata;G. Celentano
2013

Abstract

Continuous-flow organocatalyzed Diels-Alder reactions have been performed with excellent enantioselectivity for the first time in a chiral "homemade" HPLC column, packed with silica on which a MacMillan catalyst has been supported by a straightforward immobilization procedure. The versatility of the system was also proven by running with the same column continuous-flow stereoselective reactions with three different substrates, showing that the catalytic reactor may efficiently work in continuo for more than 150 h; the regeneration of the HPLC column was also demonstrated, allowing to further extend the activity of the reactor to more than 300 operating hours.
organic-synthesis; highly efficient; silyl ehers; aldehydes; reactors; cycloaddition; technology; strategies; chemistry; batch
Settore CHIM/06 - Chimica Organica
ORGANIC LETTERS
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/224245
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