Synthesis 2005(7): 1031-1048  
DOI: 10.1055/s-2005-865295
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Aza- and Diazabicyclo[X.Y.0]alkane Dipeptide Mimetics

Wolfgang Maison*, Alexander H. G. P. Prenzel
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428382495; e-Mail: maison@chemie.uni-hamburg.de;
Further Information

Publication History

Received 10 January 2005
Publication Date:
23 March 2005 (online)

Abstract

This review focuses on recent synthetic developments for the stereoselective preparation of aza- and diazabicy­clo[X.Y.0]alkane dipeptide mimetics of the general structures 1-3. Different synthetic strategies are compared with respect to stereoselectivity as well as flexibility regarding ring sizes, stereochemistry and introduction of side-chains.

  • 1 Introduction

  • 2 Azabicycloalkanes

  • 2.1 Lactam Formation

  • 2.2 Radical Cyclization

  • 2.3 Dieckmann Cyclization

  • 2.4 Iodo- and Selenocyclization

  • 2.5 Ring-Closing Metathesis

  • 2.6 N-Acyliminium Cyclization

  • 3 Diazabicycloalkanes

  • 3.1 Lactam Formation

  • 3.2 Ring-Closing Metathesis

  • 3.3 Intramolecular Reductive Amination

  • 3.4 N-Acyliminium Cyclization

  • 3.5 Tandem Cyclization

  • 4 Summary