Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes

Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes
Bruno V. M. Teodoro, Luiz F. Silva
The synthesis of homopropargylic alcohols under metal-free and mild condition is described. This transformation is based on a one-pot procedure involving sequential α-alkynylation of acyclic aldehydes using hypervalent iodine reagents and borohydride reduction. The chemistry exhibits broad substrate scope and good scalability, providing a convenient route for the α-alkynylation of aldehydes along with the formation of a quaternary carbon center. The applicability of the method is demonstrated by the gram-scale synthesis of the key synthetic precursor of botulinum toxin inhibitors.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01629

DOI: 10.1021/acs.joc.7b01629

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