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. Author manuscript; available in PMC: 2010 Sep 9.
Published in final edited form as: J Am Chem Soc. 2009 Sep 9;131(35):12550–12551. doi: 10.1021/ja9058537

Table 2.

Scope of Ni-Catalyzed Enantioselective Dienal Allylationa

graphic file with name nihms138813f5.jpg
entry substrate product yield (%)b (E,Z):(E:E) %ee
1 graphic file with name nihms138813t3.jpg graphic file with name nihms138813t4.jpg 84 >20:1 88
2 75 18:1 92
3 graphic file with name nihms138813t5.jpg graphic file with name nihms138813t6.jpg 84 >20:1 87
4 76 >20:1 90
5 graphic file with name nihms138813t7.jpg graphic file with name nihms138813t8.jpg 68 >20:1 91
6 graphic file with name nihms138813t9.jpg graphic file with name nihms138813t10.jpg 86 15:1 73
7 graphic file with name nihms138813t11.jpg graphic file with name nihms138813t12.jpg 81 7:1 85
8 graphic file with name nihms138813t13.jpg graphic file with name nihms138813t14.jpg 92 >20:1 93
9 graphic file with name nihms138813t15.jpg graphic file with name nihms138813t16.jpg 73 15:1 94
10 graphic file with name nihms138813t17.jpg graphic file with name nihms138813t18.jpg 83 16:1 90
a

For entries 1,3, and 5–10: reaction carried out in a glovebox freezer. For entries 2 and 4, reaction carried out outside glovebox and quenched by addition of 30 equiv. of acetaldehyde, followed by warming to ambient. See the SI for details.

b

Isolated yield of purified material.