Abstract
The enantiomerically pure amino ketones 13 and 31 were prepared starting from the commercially available amino diol 9 and D-serine (21), respectively. Irradiation afforded highly functionalized azetidinols 15 and 33 in a fully stereoselective manner and in high yields, whereas N-phenacylglycine 5 gave only the secondary products of a Norrish-Type-II cleavage. Compounds 15 and 33 were converted into (2R)- and (2S)-azetidine-2-carboxylic acids 20 and 37, respectively, in several steps. The influence of H-bonds on efficiency, chemo-, and stereoselectivity of the photochemical cyclization of 5, 13, and 31 was discussed. It was shown that conformational analysis of corresponding triplet biradicals is often valuable in understanding the photochemistry of amino ketones.
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