Synthesis 1976; 1976(12): 777-794
DOI: 10.1055/s-1976-24200
© 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.

The Robinson Annelation and Related Reactions

Robert E. GAWLEY*
  • *W. R. Kenan, Jr., Laboratories of Chemistry, The University of North Carolina, Chapel Hill, North Carolina 27514, U.S.A.
Further Information

Publication History

Publication Date:
12 September 2002 (online)

Annelation reactions related to the Robinson reaction are reviewed with an emphasis being placed on the regiochemistry and stereochemistry obtained in the annelation sequence. Annelations employing ring formation by a "3′-oxobutyl" side chain, or its functional equivalent are covered, and examples of experimental procedures have been selected to provide guidelines for application of a given sequence to other molecules. 1. Introduction 2. The Robinson Annelation 3. Regiochemistry of Addition to Unsymmetrical Ketones 3.1. Annelations with Enamines 3.2. Annelations using Activating or Directing Groups 3.3. Annelations using Blocking Groups 4. Stereochemistry 5. Annelations using Stabilized Electrophiles as Michael Acceptors 6. Annelations using Electrophiles with Masked Carbonyl Functions 6.1. The Wichterle Reaction 6.2. The Isoxazole Annelation 7. Annelations Involving Oxidation of Alkenyl Side Chains 8. Bis-Annelations