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. Author manuscript; available in PMC: 2012 Sep 16.
Published in final edited form as: J Org Chem. 2011 Aug 23;76(18):7614–7617. doi: 10.1021/jo2013753

Table 2.

KH-Mediated oxy-Cope Rearrangement.

Alcohola Productb Yieldc
1 graphic file with name nihms320427t11.jpg
3a
graphic file with name nihms320427t12.jpg
4a
70%
2 graphic file with name nihms320427t13.jpg
3bd
graphic file with name nihms320427t14.jpg
4b
64%
3 graphic file with name nihms320427t15.jpg
3dAre
graphic file with name nihms320427t16.jpg
4c
89%
4 graphic file with name nihms320427t17.jpg
3cAlke
graphic file with name nihms320427t18.jpg
4d
80%
5 graphic file with name nihms320427t19.jpg
3cAre
graphic file with name nihms320427t20.jpg
4e
67%
6 graphic file with name nihms320427t21.jpg
3eMef
graphic file with name nihms320427t22.jpg
4f
52%
a

Oxy-Cope rearrangement was carried out with dicyclohexyl-18-crown-6 and KH in THF.

b

Products were a mixture of α-epimers.

c

Yields are for pure isolated substances.

d

t-BuOK was used for the rearrangement.

e

Prepared by Stille coupling of the corresponding iodoalkene.

f

Prepared by Kumada coupling of the corresponding alkene.