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. Author manuscript; available in PMC: 2011 Sep 3.
Published in final edited form as: Org Lett. 2010 Sep 3;12(17):3760–3763. doi: 10.1021/ol1013476

Table 2.

Carbonylative Conjugate Addition of Et2Zn To α,β-Unsaturated Ketones.a

graphic file with name nihms227192u3.jpg
entry substrate % yield
L=PPh3 L=PCy3
1 graphic file with name nihms227192t1.jpg 82 80
2 graphic file with name nihms227192t2.jpg 81 81
3 graphic file with name nihms227192t3.jpg 84 82
4 graphic file with name nihms227192t4.jpg 79 80
5 graphic file with name nihms227192t5.jpg 86 87
6 graphic file with name nihms227192t6.jpg 52 82
7 graphic file with name nihms227192t7.jpg 67 66b
8 graphic file with name nihms227192t8.jpg 85 86
9 graphic file with name nihms227192t9.jpg 56 48
10 graphic file with name nihms227192t10.jpg 68 67
11 graphic file with name nihms227192t11.jpg 72 55c
a

Reaction with 1.3 equiv Et2Zn, 2.3 equiv TMSCl, 1 atm CO, for 4 h (7 h for entry 4; 24 h for entry 11). Subsequent to reaction, the mixture was quenched at 0 °C with acetic acid (1.5 equiv) and TBAF (1.5 equiv) for 10 minutes and then treated with saturated Na2CO3.

b

Yield adjusted to account from unremovable impurity (ca. 10%).

c

10% Pd2(dba)3, 24% ligand, and 1.95 equiv Et2Zn employed.