Functionalised trichlorosilanes in the asymmetric allylation

Kysilka, Ondřej (2013) Functionalised trichlorosilanes in the asymmetric allylation. PhD thesis, University of Glasgow.

Abstract

We present a synthetic route to the homoallylic alcohols, using the well-established asymmetric organocatalysed allylation of aldehydes. These alcohols were transformed in one step into the substituted tetrahydrofurans in the presence of achiral Lewis acids, forming three chiral centres for the price of two. A synthetic route towards chiral substituted tetrahydropyrans and unsaturated 1,5 diol-building blocks has also been developed.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: trichlorosilane, disilane, organocatalysis, organocatalyst, asymmetric synthesis, allylation, asymmetric allylation, homoallylic alcohols, tetrahydrofurans, tetrahydropyrans, dihydropyrans, diols, building blocks, asymmetric aldol reaction, axial chirality, aminal, METHOX, QUINOX, PINDY, PINDOX, Sigamide, Kenamide, natural products, Speranskatine A, Convolutamydine A
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Kocovsky, Prof. Pavel
• Date of Award: 2013
• Depositing User: Dr. Ondrej Kysilka
• Unique ID: glathesis:2013-4377
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 11 Jun 2013 10:10
• Last Modified: 11 Jun 2013 10:11
• URI: https://theses.gla.ac.uk/id/eprint/4377