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. 2020 Mar 10;59(30):12337–12341. doi: 10.1002/anie.201916004

Table 1.

Selected examples from the optimization. Inline graphic

Entry

Initiator

mol %

Time

Yield [%][a]

1

tBuOLi

10

1 h

91

2

Me3SiOLi

10

1 h

>95

3

Me3SiONa

10

<5 min

98 (70)[b]

4

Me3SiOK

10

<5 min

90

5

Me3SiONa

5

<5 min

>95

6

Me3SiONa

1

20 h

6

7

Me3SiOK

1

20 h

58

8

CsF

10

20 h

60

9

TMAF

10

20 h

trace

[a] Determined by calibrated GLC analysis with tetracosane as an internal standard. [b] Yield of isolated product on a 0.40 mmol scale after flash chromatography on silica gel in parentheses. TMAF=tetramethylammonium fluoride. graphic file with name ANIE-59-12337-g007.jpg