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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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 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: 2017-01-122017-01-12
 Publication Status: Published in print
 Pages: 257
 Publishing info: Köln : Universität zu Köln
 Table of Contents: -
 Rev. Type: -
 Identifiers: URN: urn:nbn:de:hbz:38-71485
 Degree: PhD

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