Table 10.
Asymmetric aza-Michael addition for the formation of (S)-(−)-pyrazoline.
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49 | Ar1 | Ar2 | Yield [%] | ee [%] |
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a | Ph | Ph | 77 | 92 (−) |
b | Ph | 4-MeOC6H4 | 71 | 90 (−) |
c | Ph | 4-FC6H4 | 72 | 90 (−) |
d | Ph | 4-FC6H4 | 62 | 92 (−) |
e | Ph | 2-MeOC6H4 | 89 | 92 (−) |
f | Ph | 2-MeOC6H4 | 52 | 94 (−) |
g | Ph | 2-thienyl | 66 | 87 (−) |
h | Ph | 2-thienyl | 60 | 91 (−) |
i | Ph | 3,4-(Cl)2C6H3 | 40 (62)a | 92 (−) |
j | 4-MeOC6H4 | Ph | 60 | 89 (+) |
k | 4-ClC6H4 | Ph | 70 | 88 (−) |
l | 2-MeC6H4 | Ph | 62 | 89 (−) |
m | 3-MeOC6H4 | Ph | 61 | 91 (−) |
n | 2-thienyl | Ph | 46 | 78 (−) |
aYield determined by NMR analysis of the crude reaction mixture using an internal standard.