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. Author manuscript; available in PMC: 2020 Feb 15.
Published in final edited form as: Org Lett. 2019 Jan 29;21(4):984–988. doi: 10.1021/acs.orglett.8b03959

Table 1.

Evaluation of Various Reaction Parameters a,b

graphic file with name nihms-1029763-t0007.jpg
entry Lewis acid catalyst loading (%) solvent yield (%)
3g 4g
1   B(C6F5)3 20 DCE 56 35
2   none   0 DCE 0 0
3   B(C6F5)3 10 DCE 71 22
4   B(C6F5)3 10 Et2O 83 17
5   B(C6F5)3       5.0 Et2O 22 <5
6   B(C6F5)3 10 THF 38 <5
7   B(C6F5)3 10 toluene 75 21
8   B(C6F5)3 10 benzene 81 16
9   B(C6F5)3       5.0 benzene >95 <5
10 BF3•OEt2 10 benzene 0 0
11 BPh3 10 benzene 0 0
a

Conditions: 4-methoxy-N,N,2,6-tetramethylaniline (0.1 mmol), 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.2 mmol), Lewis acid, solvent (0.25 mL), under N2, 22 °C, 12 h.

b

Yields were determined by 1H NMR analysis of unpurified product mixtures with mesitylene as the internal standard. See the Supporting Information for details.