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. 2011 Jun 23;16(6):5298–5314. doi: 10.3390/molecules16065298

Table 1.

Diastereoselective addition of phenylacetylene in the presence of ligands.

graphic file with name molecules-16-05298-i001.jpg
Entry a ligand syn% anti%
1 b -- 48 52
2 graphic file with name molecules-16-05298-i002.jpg 23 77
3 graphic file with name molecules-16-05298-i003.jpg 29 71
4 graphic file with name molecules-16-05298-i004.jpg 23 77
5 graphic file with name molecules-16-05298-i005.jpg 22 78
6 graphic file with name molecules-16-05298-i006.jpg 29 71
7 c -- 6 94

a All the reactions were performed at rt under nitrogen atmosphere Me2Zn (3 equiv.) and phenylacetylene (3 equiv.) were added to toluene in a flask under strictly anhydrous conditions, and stirred 10 min, then the ligand (20 mol%) was added and the reaction mixture and stirred for 5–10 min. Finally, the chloroketone (1 equiv.) was added. The reaction was stirred under completion (monitored by TLC, 16–24 h) and quenched with water. The dr was determined on the crude reaction mixture by 1H-NMR. b The reaction was performed in the presence of Me2Zn without ligands. c The reaction was performed with lithium phenylacetylide, prepared by the addition of 1 equiv. of n-BuLi to 1.1 equiv. of phenylacetylene at 0 °C.