Sequential regio- and diastereoselective nucleophile/electrophile addition reactions of [êta]⁶-benzaldehyde imine and [êta]⁶-benzaldehyde hydrazone tricarbonyl chromium complexes

Diplôme Thèse Sequential regio- and diastereoselective nucleophile/electrophile addition reactions of [êta]⁶-benzaldehyde imine and [êta]⁶-benzaldehyde hydrazone tricarbonyl chromium complexes eng 1993-11-09 author Liu Ronggang 24270 director Kundig Ernst Peter 26401 10.13097/archive-ouverte/unige:104743 Sc. 2637 The thesis describes the development of a new reaction sequence wich transforms aromatic compounds into regio- and stereoselectively functionalized cyclohexadienes. This is achieved through a sequential nucleophile/electrophile addition across an arene double bond. Activation to the first C-C bond forming reaction is by complexation of the arene to an electrophilic transition metal complex fragment (Cr(CO)₃). Regioselectivity is controlled by an imine substituent which directs the incoming group highly selectively to an "ortho" carbon. This combination of the use of a chiral auxiliary with organometallic methodology is highly successful and provides the basis for efficient applications in synthesis. The second step involves metal alkylation or allytation and migration of this group to the 3-position of the polyene ligand. This takes place either directly or following migratory CO insertion. An asymmetric synthesis is provided by a chiral benzaldehyde hydrazone complex. In most cases only one of the two possible diastereomers is formed. Chrome Composé organique Réaction d'addition Stéréosélectivité Dewey 540 36 Département de chimie organique 141 false b8c820ff-c7f9-4a0a-84d2-25e042501007 Thesis Public These_Liu_1993.pdf 9094463 application/pdf Restricted 2093-05-30 embargoedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Sequential regio- and diastereoselective nucleophile/electrophile addition reactions of [êta]⁶-benzaldehyde imine and [êta]⁶-benzaldehyde hydrazone tricarbonyl chromium complexes				1993	617	3

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Liu, Ronggang