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

DA reaction between cyclopentadiene 5 and various dienophiles.

graphic file with name d2sc02901d-u3.jpg
Entrya 5 t (h) Conv.b (%) 10 yieldc (%) endo : exod
1 5a 1 100 90 86 : 14
2e 5a 1
3 5b 1 100 Quant 86 : 14
4e 5b 1 9
5e 5b 3 33 27 77 : 23
6 5c 1 100 Quant 2 : 98
7 5d 4 94 90 69 : 25
16 100 96 77 : 23
8 5e 4 78 72 84 : 16
16 95 91 84 : 16
9 5f 4 54 50 91 : 9
16 72 68 89 : 11
10 5g 4 37 34 84 : 16
16 61 60 80 : 20
11 5h 2 Quant 93 >99 : 1
a

Reaction conditions: 9 (0.45 M), 5 (0.15 M), C6 and TrCl (0.039 M.) in 1.1 mL of water-saturated CDCl3, at rt.

b

Determined by 1H NMR analysis of the crude reaction mixture.

c

Isolated yield.

d

Determined by 1H NMR analysis of the crude reaction mixture according to literature data.21b,21d,27

e

The reaction was performed in the absence of C6 and TrCl.