Homopropargylic alcohols are very useful and versatile intermediates in modern organic synthesis. It is not surprising then that there have been several methods developed for the synthesis of these compounds. Despite decades of research, asymmetric propargylation not only relies heavily on stoichiometric metals and/or organometals, but few systems have been optimized for good selectivity and the substrate scope remains narrow. In contrast, we have recently developed a method of carbonyl propargylation that utilizes hydrogen transfer to couple alcohols and 1,3-enynes in the presence of catalytic amounts of iridium. Similarly, aldehydes and enynes may also be coupled in the presence of formic acid as the hydrogen source. Homopropargyl alcohols have been assembled in these manners with both high diastereo- and enantioselectivies from simple and inexpensive materials. The results of these studies, as well as the relationship between substrate and ligand structures and selectivity will be presented. 

Structure-selectivity relationships in asymmetric carbonyl propargylation via iridium catalyzed coupling of 1,3-enynes and alcohols

243rd National Meeting (2012)

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