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The use of stoichiometric amounts of chiral amino alcohol-based ligands: (a) Jiang, B.; Chen, Z. L.; Xiong, W. N. Chem. Commun. 2002, 1524.
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Catalytic procedures based on amino alcohol ligands focus on the addition of phenylacetylene to aromatic aldehydes, while few address the need to utilize functional alkynes: (a) Xu, Z.; Wang, R.; Xu, J.; Da, C.; Yan, W.; Chen, C. Angew. Chem., Int. Ed. 2003, 42, 5747.
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The method also required 1 equiv of an additional chiral sulfonamide ligand and was only applied in the addition of phenylacetylene to aromatic aldehydes below 0°C for 1-2 days: Li, X. S.; Lu, G.; Kwok, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 2002, 124, 12636.
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In this regard, one impressive example has been illustrated by the recent studies of the Carreira group, in which a catalytic version of the addition procedure could be conducted at elevated temperatures, i.e, 60°C, to overcome the kinetic barrier inhibiting protonation of the first formed Zn-alkoxide, avoiding the use of stoichiometric quantities of Zn(OTf) 2 and N-methylephedrine. See ref 3b
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