A tyrosine-derived imidazolidin-4-one was immobilized on a modified poly(ethylene glycol) and converted in situ into a soluble polymer-supported catalyst for the enantioselective Diels-Alder cycloaddition of acrolein to 1,3-cyclohexadiene (up to 92% ee) and 2,3-dimethyl-1,3-butadiene (73% ee). Catalyst recycling (up to four cycles) was accompanied by some loss of the chemical efficiency and marginal erosion of the enantioselectivity.
Poly(ethylene glycol)-supported chiral imidazolidin-4-one: An efficient organic catalyst for the enantioselective Diels-Alder cycloaddition / M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 344:2(2002), pp. 149-152. [10.1002/1615-4169(200202)344:2<149::AID-ADSC149>3.0.CO;2-U]
Poly(ethylene glycol)-supported chiral imidazolidin-4-one: An efficient organic catalyst for the enantioselective Diels-Alder cycloaddition
M. BenagliaPrimo
;G. CelentanoSecondo
;M. Cinquini;A. PuglisiPenultimo
;F. CozziUltimo
2002
Abstract
A tyrosine-derived imidazolidin-4-one was immobilized on a modified poly(ethylene glycol) and converted in situ into a soluble polymer-supported catalyst for the enantioselective Diels-Alder cycloaddition of acrolein to 1,3-cyclohexadiene (up to 92% ee) and 2,3-dimethyl-1,3-butadiene (73% ee). Catalyst recycling (up to four cycles) was accompanied by some loss of the chemical efficiency and marginal erosion of the enantioselectivity.
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