Skip to main content
. 2016 Feb 17;55(11):3734–3738. doi: 10.1002/anie.201511139

Table 3.

Grignard reagents with β‐hydrogen atoms. Inline graphic

Entry Carboxylate Grignard reagent Allene Yield [%]
1 graphic file with name ANIE-55-3734-g005.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g029.jpg 93
2 graphic file with name ANIE-55-3734-g007.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g030.jpg 68
3 graphic file with name ANIE-55-3734-g009.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g031.jpg 64
4 graphic file with name ANIE-55-3734-g011.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g032.jpg 75
5 graphic file with name ANIE-55-3734-g013.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g033.jpg 78
6 graphic file with name ANIE-55-3734-g034.jpg CyMgCl graphic file with name ANIE-55-3734-g035.jpg 71
7 graphic file with name ANIE-55-3734-g034.jpg graphic file with name ANIE-55-3734-g036.jpg graphic file with name ANIE-55-3734-g037.jpg 63
8 graphic file with name ANIE-55-3734-g038.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g039.jpg 90
9 graphic file with name ANIE-55-3734-g038.jpg graphic file with name ANIE-55-3734-g040.jpg graphic file with name ANIE-55-3734-g041.jpg 70
10 graphic file with name ANIE-55-3734-g038.jpg graphic file with name ANIE-55-3734-g042.jpg graphic file with name ANIE-55-3734-g043.jpg 61
11 graphic file with name ANIE-55-3734-g044.jpg graphic file with name ANIE-55-3734-g040.jpg graphic file with name ANIE-55-3734-g045.jpg 61
12 graphic file with name ANIE-55-3734-g021.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g046.jpg 31[b] (24)[c] 44[b] (34)[c]
13 graphic file with name ANIE-55-3734-g023.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g047.jpg 39
14 graphic file with name ANIE-55-3734-g025.jpg graphic file with name ANIE-55-3734-g028.jpg graphic file with name ANIE-55-3734-g048.jpg 25(Bz) 24(Piv) 14(Ac)

[a] Yield of product isolated from the reaction run with a 0.2 m solution of propargyl carboxylate (1–2 mmol) in Et2O, with dropwise addition of the Grignard reagent during 5 min. [b] From 0.25 mmol of substrate (R=Piv). [c] From 0.5 mmol of substrate (R=Ac).