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. Author manuscript; available in PMC: 2021 Jun 30.
Published in final edited form as: Nat Chem. 2020 Dec 30;13(3):270–277. doi: 10.1038/s41557-020-00576-z

Table 1. Summary of the effects of reaction parameters on the reaction efficiencya .

graphic file with name EMS118660-i001.jpg
Entry Variants Yield (%) e.e. (%)b
1 none 72 (69)c 92
2 L1 73 52
3 L2 76 42
4 L3 31 36d
5 L4 47 60
6 L5 37 58
7 NiBr2 52 80
8 NiBr2.diglyme 51 84
9 Ni(COD)2 31 80
10e CsF 70 68
11 PMHS 57 91
12 DMF as solvent 73 66
13 DCE as solvent n.d. n.d.
a

See the Supporting Information for section 2 experimental details; all reactions were carried out in a 0.1 mmol scale with respect to 2a; corrected GC yields using n-dodecane as an internal standard were reported.

b

The enantiomeric excesses (e.e.s) were determined using HPLC analysis of the corresponding alcohol after stereospecific oxidation of the boronic ester (see Supplementary Information section 2 for full details).

c

Isolated yield is shown in the parenthesis.

d

The opposite enantiomer was enriched.

e

Reaction time = 12h. DMF = Dimethylformamide; DCE = 1,2-Dichloroethane; RT = room temperature; h = hour. n.d. = not detected; PMHS = Polymethylhydrosiloxane; DEMS = Diethoxy-methylsilane.