Non-classical Carbocations and Enols in Asymmetric Catalysis

Pupo, Gabriele

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Non-classical Carbocations and Enols in Asymmetric Catalysis

Pupo, G. (2017). Non-classical Carbocations and Enols in Asymmetric Catalysis. PhD Thesis, Universität zu Köln, Köln.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0001-1655-7 Version Permalink: https://hdl.handle.net/21.11116/0000-000D-5BFF-F

Genre: Thesis

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Creators:
Pupo, Gabriele¹, Author

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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585

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Abstract: This thesis describes studies on non-classical carbocations and enols in asymmetric catalysis. In the first part, a novel catalytic system based on asymmetric counteranion-directed Brønsted acid organocatalysis was developed, aiming for the enantiocontrol of highly reactive intermediates such as non-classical carbocations. This challenge led to the design and fine tuning of a new class of non-nucleophilic catalysts and culminated in the first proof of concept that these intermediates can indeed be controlled asymmetrically and good enantioselectivities were obtained. In the second part, a novel activation mode for organocatalysis is presented. Its key feature is the use of a chiral Brønsted acid to promote the enolization of carbonyl compounds and to overcome some intrinsic limitations of aminocatalysis. Successfully applied to asymmetric α-alkylations (Michael addition and α-allylation) and α-oxidation reactions of ketones, this concept opens versatile and highly enantioselective new routes towards synthetically challenging quaternary and tetrasubstituted chiral centers.

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Language(s): eng - English

Dates: Accepted: 2017-01-12Date issued: 2017-01-12

Publication Status: Issued

Pages: 257

Publishing info: Köln : Universität zu Köln

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Rev. Type: -

Identifiers: URN: urn:nbn:de:hbz:38-71485

Degree: PhD

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