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. 2018 Nov 19;23(11):3023. doi: 10.3390/molecules23113023

Table 1.

Vinylation of N,O-acetal TMS ethers.

graphic file with name molecules-23-03023-i001.jpg

Entry a n M Additive Lewis Acid Solvent Yield b
1 4 Li BF3·OEt2 THF ND c
2 4 SiMe3 BF3·OEt2 CH2Cl2 ND c
3 4 MgBr BF3·OEt2 THF ND c
4 4 MgBr CuBr·SMe2 BF3·OEt2 THF 63
5 4 MgBr CuBr·SMe2 BF3·OEt2 Et2O 32
6 4 MgBr CuI BF3·OEt2 THF ND c
7 4 MgBr CuOTf BF3·OEt2 THF ND c
8 3 MgBr CuBr·SMe2 BF3·OEt2 THF 60
9 2 MgBr CuBr·SMe2 BF3·OEt2 THF 65
10 1 MgBr CuBr·SMe2 BF3·OEt2 THF ND c

a All reactions were performed using 0.3 mmol of 2 in dry solvent. See, Experimental section for a representative procedure. b Isolated yields. c Not detected.