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. Author manuscript; available in PMC: 2011 Sep 29.
Published in final edited form as: J Am Chem Soc. 2010 Sep 29;132(38):13203–13205. doi: 10.1021/ja106901u

Table 1.

Formal [2 + 2 + 2] Cycloadditions via Propargylic Ene/Cyano Diels-Alder Reactions

graphic file with name nihms-234331-t0004.jpg
entry R G conditions product yield (%)a
1 1 H H 160 °C, 21 h 5 71
2 2 CH3 H reflux, 66 h 6 96
3 2 CH3 H 140 °C, 18 h 6 55
4 3 H C≡CSiMe3 reflux, 24 h 7 30
5 4 H C≡CCH2OSit-BuMe2 reflux, 46 h 8 37
a

Isolated yield of products purified by chromatography.