Part I. A study of the alkylation chemistry of N-sulfinyl amines. Part II. Attempted preparation of the camphor imine of stereospecifically deuterated glycine.
Date of Award
Chemistry and Biochemistry
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Part I. N-sulfinyl-n-butylamine 26 and N-sulfinyl-n-pentylamine 34 were prepared according to the literature. Alkylation reactions using LDA as the base were performed on compounds 26 and 34 using benzylic and simple alkyl halides as the alkylating agent. No useful products were obtained using simple alkyl halides, but compounds 32, 33, 35, and 36 were isolated when benzyl bromide was used. These are the result of sulfur anion attack on the alkyl halide. Compounds 32, 33, 35, and 36 were subjected separately to cycloaddition reactions with 2,3-dimethylbutadiene. Compound 37 was the product isolated ($>$93%) from each cycloaddition reaction regardless of the dienophile used. Aldol reactions with compounds 26 and 34 under a variety of conditions using aldehydes and ketones were unsuccessful. Part II. Chiral mono-deuterated (2-$\sp2$H$\sb1\rbrack$ glycine was prepared according to the literature with 76% ee. Attempts to esterify the chiral glycine without racemizing the chiral center were unsuccessful. Racemization occurred when trying to deblock the CBZ-derivative of the amino ester using Pd-C/H$\sb2$(g) hydrogenation conditions. The camphor imine of isopropyl glycinate was deprotonated with LDA and then quenched with a variety of deuterating agents. Incomplete deuterium incorporation was observed in all cases. A rationale for this result is proposed. Source: Masters Abstracts International, Volume: 30-03, page: 0750. Thesis (M.Sc.)--University of Windsor (Canada), 1990.
Ammoscato, Vince., "Part I. A study of the alkylation chemistry of N-sulfinyl amines. Part II. Attempted preparation of the camphor imine of stereospecifically deuterated glycine." (1990). Electronic Theses and Dissertations. 3002.