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. Author manuscript; available in PMC: 2012 Nov 4.
Published in final edited form as: J Org Chem. 2011 Oct 7;76(21):8944–8954. doi: 10.1021/jo201658y

Table 2.

Retro-[4+2]/[4+2] reactions to afford bicyclo[2.2.2]-octenonesa

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entry dienophile (equiv) cycloadductb yieldc (%)
1 graphic file with name nihms328284t1.jpg
9a
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10a
85
2 graphic file with name nihms328284t3.jpg
9b
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10b
99
3 graphic file with name nihms328284t5.jpg
9c
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10cd
98
4 graphic file with name nihms328284t7.jpg
9d
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10d
85
5 graphic file with name nihms328284t9.jpg
9e
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10ed
76
6 graphic file with name nihms328284t11.jpg
9f
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10f
90
7 graphic file with name nihms328284t13.jpg
9g
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10gd
80
a

Reaction conditions: dimer (−)-2, dienophile, SiC chip, mesitylene, μW, 180 °C, 15 min;

b

Single diastereomer isolated unless otherwise noted;

c

Isolated yield after column chromatography;

d

Approximately 9% of an inseparable minor product observed by 1H-NMR (ca. 10:1 isomeric ratio).