Synlett 1991; 1991(5): 317-318
DOI: 10.1055/s-1991-34728
letter
© 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.

New Sequential Carbon-Carbon Bond Forming Reactions. A Samarium(II) Iodide Mediated Vinylogous Barbier Reaction Followed by an Aldol Reaction

Dennis P. Curran* , Ronald L. Wolin
  • *Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
Further Information

Publication History

Publication Date:
07 March 2002 (online)

Reduction of 4-(3-iodopropyl)cyclopent-2-en-1-ones 1 and 7 with 2.5 equivalents of samarium(II) iodide in tetrahydrofuran containing 10 equivalents of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) produces bicyclic samarium enolates that can be protonated to give simple bicyclo[3.3.0]octan-3-ones, or reacted with aldehydes to give functionalized bicyclo[3.3.0]octan-3-ones. Depending on the structure of the aldehyde, a rapid intramolecular Tishchenko reaction may follow the aldol reaction.