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. 2016 Nov 2;72(50):8294–8308. doi: 10.1016/j.tet.2016.10.073

Table 1.

Cycloaddition of the nitrones 20a-20e and allyl alcohol.

Nitrone Nucleobase B Reaction time (h)a,b cis/trans ratio 21:22 Yield (%)
20a graphic file with name fx2.gif 24a
2.5b
64:36a
69:31b
21a – 47c; 22a – 28c
21a – 68c; 22a – 25c
20b graphic file with name fx3.gif 15b 69:31 21b–44c; 22b–21c
20c graphic file with name fx4.gif 46a
5b
91:9
91:9
21c – 21c; 21c + 22c – 21d
21c – 26c; 21c + 22c – 22d
20d graphic file with name fx5.gif 7.5b 74:26 21d–37c; 21d + 22d–12d; 22d–22c
20e graphic file with name fx6.gif 5b 83:17 21e – 21c; 21e + 22e – 26d
a

The cycloaddition reaction was conducted at 60 °C.

b

The cycloaddition reaction was conducted under MW irradiation.

c

Yield of the pure diastereoisomer.

d

Yield of a pure mixture of diastereoisomers.