PhD ceremony Mr. B. Mao: Catalytic asymmetric synthesis of butenolides and γ-butyrolactones

PhD ceremony: Mr. B. Mao, 14.30 uur, Academiegebouw, Broerstraat 5, Groningen

Dissertation: Catalytic Asymmetric Synthesis of Butenolides and γ-Butyrolactones

Promotor(s): prof. B.L. Feringa

Faculty: Mathematics and Natural Sciences

Chiral butenolides and γ-butyrolactones are key structural and ubiquitous moieties in many natural products and biologically active compounds. The stereochemical information of those compounds is often recognized to be the key to their effectiveness as a bioactive compounds. Thus the efficient construction of chiral butenolides and γ-butyrolactones has attracted considerable attention in the recent years, especially in the context of the development of sustainable chemistry for the future.

This thesis describes the application of copper-catalyzed asymmetric allylic alkylation, palladium-catalyzed asymmetric allylic alkylation and γ-allylation for the construction of key carbon­–carbon and carbon–heteroatom bonds of butenolides and γ-butyrolactones. A second topic in the thesis comprizes diversity oriented synthesis of highly functionalized chiral cyclic and bicyclic esters through copper catalyzed hetero-allylic asymmetric alkylation followed by cyclization or cycloaddition.