A Convenient Preparation of Diastereomerically Pure, Diversely Substituted Piperazine-2,5-diones from N-Protected α-Amino Acids
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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.
© 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
Organic Chemical Synthesis