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. 2022 Jul 7;13(29):8618–8625. doi: 10.1039/d2sc02901d

DA reaction between 2,3-dimethylbutadiene 7 and various dienophiles.

graphic file with name d2sc02901d-u2.jpg
Entrya 5 Conv.b (%) 8 yieldc (%)
1 5a 82 75
2 5b 100 82
3 5c 80 73
4 5d 32 27
5 5e 7 5
6 5f 16 16
7d 5f 34 27
8 5g 61 60
9 5h 100 92
a

Reaction conditions: 7 (0.45 M), 5 (0.15 M), C6 and TrX (0.039 M) in 1.1 mL of water-saturated CDCl3, at rt for 16 h.

b

Determined by 1H NMR analysis of the crude reaction mixture according to literature data.21a,b,26

c

Isolated yield.

d

The reaction was carried out at 50 °C.