PubMed · 13298630
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E ASMUSSEN. 1955. The acetylene method.. https://pubmed.ncbi.nlm.nih.gov/13298630/
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The asymmetric addition of phenylacetylene to aldehydes was carried out by using a camphorsulfonamide titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the products with good yields and high ees. This system is very useful for the synthesis of chiral propargylic alcohol. [reaction: see text]
After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles. [reaction: see text]
[structure: see text] The BINOL-Salen compound (-)-1 can catalyze the addition of both aryl- and alkylalkynes to aromatic aldehydes at room temperature with high enantioselectivity (86-97% ee). The conditions for this catalytic process are both mild and simple. Unlike most other BINOL-based catalysts, using ligand (-)-1 not only avoids heating or cooling but also does not require the addition of Ti(O(i)Pr)(4).