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Synlett 2000; 2000(7): 1004-1006
DOI: 10.1055/s-2000-6652
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A Straightforward Approach Towards Substituted cis Hydroxyprolines

Heike Mues* , Uli Kazmaier
  • *Organisch-Chemisches Institut der Universität, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany; Fax + 49(62 21)54 42 05; E-mail: ck1@ix.urz.uni-heidelberg.de
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Publication Date:
31 December 2000 (online)

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Allylic esters of TFA-protected amino acids undergo asymmetric Claisen rearrangements in the presence of cinchona alkaloids, giving rise to γ,δ-unsaturated amino acids in a highly stereoselective fashion. Subsequent iodolactonization, bicyclization and opening of the lactone ring with nucleophiles such as amino acids or peptides provides hydroxyproline derivatives directly incorporated into peptides.

amino acids - Claisen rearrangements - iodolactonization - peptides - proline