Development of novel enantioselective catalytic reactions

Kabeshov, Mikhail A. (2008) Development of novel enantioselective catalytic reactions. PhD thesis, University of Glasgow.

Abstract

The inverse electron demand Diels-Alder reaction between 2-pyrone-3-carboxylic acid and various vinyl ethers has been performed to attain the respective products with very high diastereoselectivity, which can be used for the synthesis of cycloheixenyl nucleosides (Scheme 1). [diagram]. Scheme 1. Highly diastereoselective Inverse Electron Demand Diels-Alder reaction Primary amino alcohols derived from natural amino acids have been found to be efficient organocatalysts for the cross-aldol reaction between acetone and activated ketones, affording the respective products with high enantioselectivity (Scheme 2). [diagram]. Scheme 2. The enantioselective cross-aldol reaction catalysed by leucinol A practical, highly stereoselective, two-step protocol for the alpha-allylation of aldehydes, starting from allyltrichlorosilanes, has been developed. As a result of the kinetic resolution in each step, virtually enantio- and geometrically pure linear homoallylic alcohols were obtained in high yield from the technical grade aliyltrichlorosilanes by using only 5 mol% of a chiral catalyst (Scheme 3). [diagram]. Scheme 3. The highly enantioselective alpha-allylation of aldehydes.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Advisers: Pavel Kocovsky; Andrei Malkov
• Keywords: Organic chemistry, enantioselective catalysis, catalysts.
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Kocovsky, Prof. Pavel and Malkov, Prof. Andrei
• Date of Award: 2008
• Depositing User: Enlighten Team
• Unique ID: glathesis:2008-71110
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 10 May 2019 10:49
• Last Modified: 11 Jul 2021 09:57
• Thesis DOI: 10.5525/gla.thesis.71110
• URI: https://theses.gla.ac.uk/id/eprint/71110