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  • A Convenient Preparation of Diastereomerically Pure, Diversely Substituted Piperazine-2,5-diones from N-Protected α-Amino Acids

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    Author
    Nikulnikov, Mikhail
    Shumsky, Alexei
    Krasavin, Mikhail
    Year published
    2010
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    Abstract
    The products of the Ugi reaction of various N-tert-but�y�rbonyl-protected a-amino acids, aldehydes, amines and tert-butyl isocyanide, after tert-butoxycarbonyl deprotection, undergo efficient microwave-assisted cyclization in acetic acid to give dia�ereomerically pure, racemic piperazine-2,5-diones. The formation of a single diastereomer is rationalized via an enolization equilibration process in acetic acid at high temperature which enriches the product mixture in the more stable diastereomer. The relative ste�o�emistry of the products are confirmed by NOESY experiments and are consistent with molecular mechanics calculations.The products of the Ugi reaction of various N-tert-but�y�rbonyl-protected a-amino acids, aldehydes, amines and tert-butyl isocyanide, after tert-butoxycarbonyl deprotection, undergo efficient microwave-assisted cyclization in acetic acid to give dia�ereomerically pure, racemic piperazine-2,5-diones. The formation of a single diastereomer is rationalized via an enolization equilibration process in acetic acid at high temperature which enriches the product mixture in the more stable diastereomer. The relative ste�o�emistry of the products are confirmed by NOESY experiments and are consistent with molecular mechanics calculations.
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    Journal Title
    Synthesis
    Volume
    15
    DOI
    https://doi.org/10.1055/s-0029-1218829
    Copyright Statement
    © 2010 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com
    Subject
    Organic Chemical Synthesis
    Publication URI
    http://hdl.handle.net/10072/48041
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