Download PDF
Synlett 2001; 2001(Special Issue): 0910-0913
DOI: 10.1055/s-2001-14664
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.

Lewis Acid Catalyzed Reaction of Aromatic Vinyl Halides with Aromatic Aldehydes: A Novel Aldol-type Condensation Mimic

Philip W. H. Chan* , Shin Kamijo, Yoshinori Yamamoto
  • *Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan; Fax + 81-22-217-6784; E-mail: yoshi@yamamoto1.chem.tohoku.ac.jp
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download Permissions and Reprints All articles of this category

In the presence of catalytic amounts of Lewis acid, aromatic α-vinyl halides readily undergo reaction with aromatic aldehydes at ambient temperatures to give a variety of substituted trans-chalcones in moderate to excellent yields. These compounds are potentially useful synthetic intermediates for organic synthesis as well as compounds of significance in terms of their ability to exhibit a wide spectrum of biological activity. This is the first reported example in which haloalkenyl derivatives other than metallooxyalkenes can participate in the Mukaiyama-aldol type carbon-carbon formation reaction.

Lewis acid - catalysis - α-halostyrenes - aromatic aldehydes - substituted trans-chalcones