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. Author manuscript; available in PMC: 2011 Oct 15.
Published in final edited form as: J Org Chem. 2010 Oct 15;75(20):6793–6805. doi: 10.1021/jo100907u

Table 5.

Seven-membered enaminone preparation

entry ynonea enaminone methodb yieldc
1 graphic file with name nihms-225144-t0031.jpg 2u graphic file with name nihms-225144-t0032.jpg 3u A 60
B 64
2 graphic file with name nihms-225144-t0033.jpg 2v graphic file with name nihms-225144-t0034.jpg 3v A 64
B 63
3 graphic file with name nihms-225144-t0035.jpg 2w graphic file with name nihms-225144-t0036.jpg 3w A 81
B 84
4 graphic file with name nihms-225144-t0037.jpg 2x graphic file with name nihms-225144-t0038.jpg 3x A 66
B 65
a

See Supporting Information for the synthesis of ynones 2u–2x.

b

Method A: i) 4N HCl/dioxane, 15 min. ii) K2CO3, MeOH; Method B: i) Nal (3 equiv), formic acid, 6–24 h. ii) K2CO3, MeOH;

c

Isolated yield.