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. Author manuscript; available in PMC: 2015 Sep 8.
Published in final edited form as: Chemistry. 2014 Jul 30;20(37):11726–11739. doi: 10.1002/chem.201402353

Table 2.

One-pot synthesis of α-substituted ketones via tandem allylic substitution/oxidation.

graphic file with name nihms626785u2.jpg
Entry Allyl acetate α-Substituted ketones Yield (%)[a]
1 1a graphic file with name nihms626785t29.jpg 3a 85
2 1a graphic file with name nihms626785t30.jpg 3b 82
3 1a graphic file with name nihms626785t31.jpg 3c 81
4 1a graphic file with name nihms626785t32.jpg 3d 75
5 1f graphic file with name nihms626785t33.jpg graphic file with name nihms626785t34.jpg 3e 65
6 1f 3e 78[b]
[a]

Yield of purified and isolated products.

[b]

Allylic substitution carried out with Pd(OAc)2 (5 mol %) and PPh3 (10 mol %) at rt, and oxidation carried out with 3 equiv of NaBO3·H2O in THF/H2O (1:1) at rt.