Font Size: a A A

Zinc-mediated ?-regioselective Cinnamylation Reaction

Posted on:2018-09-14Degree:MasterType:Thesis
Country:ChinaCandidate:H S GaoFull Text:PDF
GTID:2321330536957171Subject:Chemistry
Abstract/Summary:PDF Full Text Request
The ?-cinnamylated structural unit componds are of great importance in organic synthesis,pharmaceuticals,and bioactive products.?-Cinnamylated alcohols,in particular,are synthetically and biologically relevant,not only for their presence as the prevalent structure in many biologically active natural products but also because they have been proven to be useful intermediates.But there is a considerable difficulty in controlling the ?-regioselectivity of the addition in the cinnamylation reaction.This paper studies the ?-regioselectivity problem and develops a method to guarantee a perfect comtrol of the ?-regioselectivity during the addition of the cinnamylmetal to C=O,C=C-C=O.The first chapter of the paper introduces the status of the addition reaction of C = O,C=C-C=O and allyl metal halides,analyese the problem and drawback and learn from the previous research for this article to provide the meaning of the topic and innovation.The second chapter describes the synthetic methods ?-cinnamylated alcohols the cinnamylation reaction of aldehydes,ketones and bisallylic alcohols via the cinnamylation reaction of esters.Highly selective high allyl alcohol compounds are produced by one pot in cheap and readily available THF and a possible mechanism was proposed.The third chapter describes the direct access to selectivity addition products via the cinnamylation reaction of ?,?-unsaturated carbonyl compounds.The raction could get highly ?-regioselectivity and highly 1,4-selectivity products via changing the acidity of the system,and a possible mechanism was proposed.All of the compounds obtained by the above mentioned reactions were characterized by 1H NMR,13 C NMR and HRMS.
Keywords/Search Tags:C innamylation, Unstaturated bonds, Regioselectivity
PDF Full Text Request
Related items