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. Author manuscript; available in PMC: 2019 Aug 1.
Published in final edited form as: J Am Chem Soc. 2018 Jul 18;140(30):9392–9395. doi: 10.1021/jacs.8b05725

Table 1.

Correlation between Aldehyde Electrophilicity and Enantioselectivity in the anti-(α-Aryl)allylation of Aromatic Aldehydes and Fluoral Hydrate.a

graphic file with name nihms-993314-t0004.jpg
Entry R σ 1a-1i 3a-3h Yield% dr ee%
1 4-Me2N-Ph -0.83 1a 3a 16 4:1 1
2 4-MeO-Ph -0.27 1b 3b 54 9:1 5
3 4-Me-Ph -0.17 1c 3c 69 4:1 12
4 Ph 0.00 1d 3d 74 4:1 15
5 4-F-Ph 0.06 1e 3e 88 3:1 16
6 4-Br-Ph 0.23 1f 3f 88 4:1 23
7 3-(6-Br-Pyr) - 19 3g 82 5:1 37
8 2-(6-Br-Pyr) - 1h 3h 75 4:1 65
9b CF3 - 1i 4b 88 >20:1 94
a

Yields of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis. See Supporting Information for further experimental details.

b

4Å molecular sieves 300 wt%). Fluoral hydrate in water (75 wt%).