Table 15.
Enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides.
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67 | R1 | R2 | Ar | Yield [%] | ee [%]a |
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a | Me | H | Ph | 65 | 87 |
b | Et | H | Ph | 51 | 81 |
c | Pr | H | Ph | 50 | 81 |
d | Ph | H | Ph | 77 | 54 |
e | Pr | H | Ph | 78 | 89 |
f | Me | Me | Ph | 66 | 62 |
g | Me | H | p-MeC6H4 | 62 | 88 |
h | Me | H | p-MeOC6H4 | 74 | 84 |
i | Me | H | p-ClC6H4 | 43 | 48 |
j | Me | H | p-O2NC6H4 | 47 | 89 |
k | Me | H | o-MeOC6H4 | 81 | 94 |
l | Me | H | o-ClC6H4 | 94 | 96 |
m | Me | H | o-BrC6H4 | 43 | 90 |
n | Me | H | m-MeOC6H4 | 20 | 25 |
o | Me | H | m-ClC6H4 | 36 | 81 |
p | Me | H | m-O2NC6H4 | 56 | 77 |
q | Pr | H | p-MeOC6H4 | 75 | 79 |
r | Pr | H | p-ClC6H4 | 78 | 88 |
s | Pr | H | p-O2NC6H4 | 80 | 86 |
t | Pr | H | o-ClC6H4 | 76 | 92 |
u | Pr | H | m-MeOC6H4 | 82 | 82 |
v | Pr | H | m-ClC6H4 | 80 | 88 |
w | Pr | H | Ph | 71 | 86 |
aDetermined by HPLC using a chiral stationary phase.