Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes |
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Authors: | Liu Lei Wang Rui Kang Yong-Feng Chen Chao Xu Zhao-Qing Zhou Yi-Feng Ni Ming Cai Hua-Qing Gong Mao-Zhen |
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Institution: | Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu 730000, China. |
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Abstract: | The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols. |
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