Synthesis 2011(6): 954-960  
DOI: 10.1055/s-0030-1258428
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Practical One-Pot Double Functionalizations of Proline

Peter Huy, Hans-Günther Schmalz*
Department für Chemie, Universität zu Köln, Greinstr. 4, 50939 Köln, Germany
Fax: +49(221)4703064; e-Mail: schmalz@uni-koeln.de;
Further Information

Publication History

Received 23 December 2010
Publication Date:
10 February 2011 (eFirst)

Abstract

Solubilization of proline as the triethylammonium salt allows N-protection (as the Boc, Cbz or Moc derivative) and subsequent esterification or amidation of the carboxy terminus to be performed in an efficient one-pot fashion. Based on this concept, highly practical protocols were developed to prepare a series of proline derivatives (including Pro-Ser dipetides, Weinreb amides and N-protected proline esters), which are important intermediates, for instance, for the synthesis of proline-derived peptides, chiral reagents and catalysts for asymmetric synthesis.