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Organocatalytic Domino Reactions
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2007 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Organocatalyzed reactions involving activation strategies of ketones and aldehydes are important processes in organic chemistry. These activation strategies serve as a versatile platform for the construction of several domino reactions. This thesis describes the development of six new asymmetric or-ganocatalyzed domino reactions for the enantioselective formation of carbo-cycles or heterocycles. The domino reactions are based on two major activation pathways the domino “iminium-enamine” and the domino “enamine-iminium”. Making use of the domino “iminium-enamine” reaction, 2H-1-benzopyrans, 2H-1-benzothiopyrans and 1,2-dihydroquinolines and cyclopropanes can be obtained in high yields and excellent ee´s. Via the amine-catalyzed domino “enamine-iminium” reaction the synthesis of aza-Diels-Alder and Diels-Alder products can be achieved with high ee´s and yields. Moreover, a mechanistic model is proposed for each reaction that enables the stereochemical outcome of the reaction to be predicted.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi , 2007. , 67 p.
Keyword [en]
organocatalytic, domino, iminium-enamine, enamine-iminium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-6839ISBN: 978-91-7155-450-5 (print)OAI: oai:DiVA.org:su-6839DiVA: diva2:197171
Public defence
2007-06-08, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2007-05-16 Created: 2007-05-04Bibliographically approved

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