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Organocatalytic asymmetric alkenylation

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Organocatalytic Asymmetric Alkenylation of Carbonyl Compounds by Nikolay S. Kondratyev DOCTORAL THESIS Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University 30 September 2019 © By Nikolay Kondratyev 2019 Abstract Asymmetric alkenylation of carbonyl compounds using organocatalysed reaction with respective organoelement reagents has developed into a useful and practically important method for the synthesis of enantiomerically enriched homoallylic amines and alcohols. As Type 1 reagents, secondary allylboronates and linear γ-functionalised allyltrichlorosilanes transfer stereochemical information (chirality or E/Z configuration) into the product (Scheme, reactions 1 and 2). Scheme The first reaction leads to synthetically important, unprotected Z-homoallylic amines which were previously inaccessible by direct methods. These compounds can serve as useful synthetic building blocks for syntheses of alkaloids and other natural, medicinal and bioactive compounds. The second reaction is the key step in the preparation of chiral cis-vinyl epoxides, a structural motif that was employed in the total synthesis of prostaglandins and other bioactive compounds. The first chapter of this thesis describes a novel, highly efficient kinetic resolution method of a novel class of chromatographically-stable chiral secondary crotylboronates, and their application for a practical, direct synthesis of unprotected (S,Z)-homoallylic ...
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