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Synthesis 2003(5): 0785-0789
DOI: 10.1055/s-2003-38062
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Indium-Mediated Allenylation and Propargylation of Allenic Alcohols with Prop-2-ynyl Bromides

Weishi Miao, Tak Hang Chan*
Department of Chemistry, McGill University, Montreal, Quebec, H3A 2K6, Canada
Fax: +1(514)3983797; e-Mail: tak-hang.chan@mcgill.ca;
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Publication History

Received 15 February 2003
Publication Date:
21 March 2003 (online)

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Abstract

Indium was found to mediate the reaction between aldehydes and 1-bromo-2-butyne to give E-1-substituted-2,5-dimethyl-heptatrien-1-ol compounds in moderate to good yields. The reaction was extended to the regio- and stereoselective allenylation and propargylation of allenic alcohols with different prop-2-ynyl bromides in the presence of indium and indium tribromide under ultrasonic irradiation.

Key words

indium - allenylation - propargylation - allenic alcohols - prop-2-ynyl bromides

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