Dimethylprolinol Versus Diphenylprolinol in CuBr₂-Catalyzed Enantioselective Allenylation of Terminal Alkynols

Abstract

The CuBr₂-catalyzed enantioselective allenylation of terminal alkynols with carbon chains of different lengths has been developed. Compared with (S)-α,α-diphenylprolinol, the reaction using (S)-α,α-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.

Key words

CuBr₂ - enantioselective allenylation - terminal alkynols - (S)-α,α-diphenylprolinol - (S)-α,α-dimethylprolinol - phlomic acid

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