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Microwave-Assisted Synthesis of Guanidine Organocatalysts Bearing a Tetrahydroisoquinoline Framework and Their Evaluation in Michael Addition Reactions
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
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2012 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 17, 3331-3337 p.Article in journal (Refereed) Published
Abstract [en]

The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and beta-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee).

Place, publisher, year, edition, pages
2012. no 17, 3331-3337 p.
Keyword [en]
Organocatalysis, Michael addition, Microwave chemistry
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-176811DOI: 10.1002/ejoc.201200303ISI: 000304529100015OAI: oai:DiVA.org:uu-176811DiVA: diva2:537735
Available from: 2012-06-27 Created: 2012-06-26 Last updated: 2013-11-20Bibliographically approved

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Arvidsson, Per I.
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