Synthesis 1994; 1994(6): 535-551
DOI: 10.1055/s-1994-25519
review
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Asymmetric Hetero Diels-Alder Reactions

Herbert Waldmann*
  • *Institut für Organische Chemie der Universität Karlsruhe, Richard-Willstätter-Allee 2, D-76128 Karlsruhe, Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

Asymmetric hetero Diels-Alder reactions provide a multitude of opportunities for the highly efficient regio- and stereoselective construction of various heterocycles in enantiomerically pure form. Despite the great potential of this synthetic methodology, its development was for a long time restricted to only a few efforts. However, during the last decade this field has been the subject of intense and successful activities. This review summarizes the progress which has been made in the development of efficient chiral auxiliary groups and catalysts for the steric steering of aza, oxa and thia Diels-Alder cycloadditions and thereby describes the current state of the art. 1. Introduction 2. Aza Diels-Alder Reactions 2.1. Imino Dienophiles and Dienes 2.1.1. C- and N-Acylimines and N-Acylazo Compounds as Dienophiles and Dienes 2.1.2. Imines and Iminium Salts as Dienophiles and Dienes 2.2. N-Sulfinyl Dienophiles 2.3. Nitroso and Nitro Dienophiles and Dienes 2.3.1. Nitroso Compounds as Dienophiles 2.3.2. Nitroso Compounds as Dienes 2.3.3. Nitro Compounds as Dienes 3. Oxa Diels-Alder Reactions 3.1. Carbonyl Dienophiles 3.2. Oxabutadienes 4. Thia Diels-Alder Reactions 5. Miscellaneous 6. Conclusion