Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines
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A four-center, three-component Ugi-type reaction of a variety of keto acids, Boc- or Cbz-protected hydrazine, and isocyanides offers a simple and high yielding access to cyclic products containing an N-aminolactam unit. The latter are shown to form consistently an intramolecular hydrogen bond leading to a ߭turn-like secondary structure. The possibility of integrating such N-aminolactam units (without disruption of the folded structure) into pseudotripeptide fragments is demonstrated.
© 2010 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
Organic Chemical Synthesis