An In-Mediated Tandem Reaction of Aldehydes with 3-Bromo-1-propyne To Produce 1-Substituted-3-methylene-5-yn-1-ol Compounds

A one‐pot reaction for the synthesis of 1‐substituted‐3‐methylene‐5‐yn‐1‐ol compounds from In‐mediated propargylation of aldehydes with 3‐bromo‐1‐propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the tr...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-01, Vol.2008 (2), p.295-298
Main Authors: Huang, Jing-Mei, Luo, Hui-Chao, Chen, Zu-Xing, Yang, Gui-Chun, Loh, Teck-Peng
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Alkynes
Indium
Propargylation
Tandem
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Summary:A one‐pot reaction for the synthesis of 1‐substituted‐3‐methylene‐5‐yn‐1‐ol compounds from In‐mediated propargylation of aldehydes with 3‐bromo‐1‐propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700758