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. Author manuscript; available in PMC: 2022 Feb 23.
Published in final edited form as: Angew Chem Int Ed Engl. 2019 Feb 11;58(10):3198–3202. doi: 10.1002/anie.201900228

Table 1:

Catalyst optimization: Effects of ligands and solvents.[a]

graphic file with name nihms-1779912-t0003.jpg
Entry Ligand Solvent T [°C] Yield [%] ee [%]
1 iPr-biOx DMPU 25 52 83
2 iBu-biOx DMPU 25 69 89
3 Cy-biOx DMPU 25 41 87
4 tBu-biOx DMPU 25 28 0
5 Ph-biOx DMPU 25 25 0
6 4-hept-biOx DMPU 25 64 73
7 indane-biOx DMPU 25 52 64
8 Ph-box DMPU 25 0 –
9 iPr-pyrox DMPU 25 30 28
10 iPr-pybox DMPU 25 5 –
11 iBu-biOx DMPU 10 38 90
12 iBu-biOx DMPU/THF (3:1) 10 74 90
13 iBu-biOx DMPU/THF (1:1) 10 90 91
14 iBu-biOx DMPU/THF (1:3) 10 28 91
[a]

Reaction conditions: 1 (0.2 mmol, 1 m), PhBr (4 m). Yields determined by 1H NMR spectroscopy using mesitylene as an internal standard; ee values determined by HPLC analysis on a chiral stationary phase.

[a]