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Investigation of the Stereoselectivity in the Staudinger Reaction

Author: LiuMingShun
Tutor: FuNanYan
School: Fuzhou University
Course: Organic Chemistry
Keywords: Staudinger reaction beta - lactam Diazoketone Wolff rearrangement Stereoselective
CLC: O621.25
Type: Master's thesis
Year: 2010
Downloads: 77
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Abstract


The ketene and imine [2 2] cycloaddition reaction of a beta-lactam, which is called the Staudinger reaction. This is to commemorate the 1907 German chemist Hermann Staudinger first discovered this type of reaction. Staudinger reaction discovery has now been more than 100 years, but it is still one of the most important and most commonly used method of synthesis of beta-lactam compounds. beta-lactams are a class of very important and a compound having biological activity. As the widely used value of antibiotics, design synthesis and stereochemistry of these compounds, has been front and one of the hot areas of synthetic organic chemistry research. An outline of the structure of beta-within amide, classification and synthesis methods, the ferrocene-containing beta-lactam research progress, and outlines the important role of the adamantane derivatives in the biomedical field. On this basis, the paper diazo ketone as a ketene precursor Wolff rearrangement caused by heating to produce enone intermediate imine substituted with various electronic effects 2 [2 2] Ring Addition Reaction, the stereoisomeric product was characterized using 1H NMR spectra to obtain a series dominated by the trans form of the beta-lactam product, and its perspective selection result are discussed. The main contents are as follows: reaction of ferrocene replace diazoketone. Of ferrocene diazo ketone 1a and 5 the imine 2 [2 2] cycloaddition to give a series of space on the presence of cis-trans isomers of beta-lactam compound 3a-e, in a yield of 50 - 86%. Six unknown compounds isolated use of IR, 1H NMR, 13C NMR, MS, HRMS characterization of some of these compounds were characterized by elemental analysis to determine its structure. 2 of benzene and substituted diazo ketones. Three of benzene and substituted diazo ketone 1b-d and imine 2 [2 2] cycloaddition to give a series of space exists on the cis-trans isomers of beta-lactam compound 3f-s, yield 36-83%. 17 compounds isolated by IR, 1H NMR characterization of some unknown compounds the use of 13C NMR, MS, HRMS carried out to characterize the structures determined. Adamantane substituted diazo ketones. A diazo ketone 1e adamantane and 5 imine 2 [2 2] cycloaddition to give a series of space on the presence of cis-and trans beta-lactam compound 3T-x, the production rate of 7-82. %. Separation to five unknown compounds using IR, 1H NMR, 13C NMR, MS, HRMS were characterized to determine its structure. 4 for discussion through stereo cis-trans isomerization of the above three types of reaction results obtained ketene and imine substituent electronic effects and spatial effect of the Staudinger reaction stereoselectivity correspondence relationship, so as to achieve stereoselectivity of the Staudinger reaction control to provide experimental basis.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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