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The CuBr 2 -catalyzed enantioselective allenylation of terminal alkynols with carbon chains of different lengths has been developed. Compared with (S)-alpha,alpha-diphenylprolinol, the reaction using (S)-alpha,alpha-dimethylprolinol as the chiral amine afforded optically active 1,3-disubstuted allenols with higher ee -values. Both aliphatic and aromatic aldehydes could be applied. The naturally occurring phlomic acid was synthesized in four steps from commercially available hex-5-yn-1-ol.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI