ChemInform Abstract The title compound (IX) is prepared starting from the Grignard reagent (I) (easily built up from phenol and 1,9-nonanediol) and the optically active oxirane (II); the latter determines the first stereogenic center. The key steps are the photolactonization of (V), the formation of the second stereogenic center by stereoselective reduction of the ketone (VII) using Yamamoto's reagent, and the pyridine-accelerated dihydroxylation of (VIII) to form the last two stereogenic centers. A second reaction pathway to the title compound is also investigated and the X-ray structures are given for a variety of intermediates, such as (VI) (space group Pcab, Z = 8), the acetate derived from (VIII) (P21/c, Z=4) and the triacetate of (IX) (P212121, Z=4).
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SummaryA series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.
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