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. Author manuscript; available in PMC: 2010 Jun 28.
Published in final edited form as: J Am Chem Soc. 2005 Apr 27;127(16):5776–5777. doi: 10.1021/ja051180l

Table 2.

[4 + 2] Cycloadditions of Conjugated Enynamides with Alkynes

entry ynamide conditionsa indoline yield (%)b
graphic file with name nihms-214833-t0008.jpg
1 25 (R = Me) 110 °C, 8 h 30 96
2 25 (R = Me) 110 °C, 8 hc 30 80
3 25 (R = Me) 110 °C, 8 hd 30 72
4 25 (R = Me) 0 °C to rt, 3 he 30 78
5 26 (R = t-Bu) 110 °C, 8 h 31 91
graphic file with name nihms-214833-t0009.jpg graphic file with name nihms-214833-t0010.jpg
6 27 (R = SiMe3) 180 °C, 16 h 32 86
7 28 (R = CO2Me) 110 °C, 30 h 33 95
8 29 R = C≡CC(Me)2OSi(i-Pr)3) 110 °C, 30 h 34 84
a

Cycloadditions performed in toluene (0.05 M) with 1 equiv of BHT unless otherwise indicated.

b

Isolated yields.

c

Reaction in the absence of BHT.

d

Reaction in TFE (0.05 M) without BHT.

e

Reaction in the presence of 2.5 equiv of Me2AlCl in CH2C12 (0.05 M) without BHT.