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Synlett 2001; 2001(Special Issue): 0910-0913
DOI: 10.1055/s-2001-14664
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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
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Publication Date:
31 December 2001 (online)

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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

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