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. 2021 Oct 18;17:2585–2610. doi: 10.3762/bjoc.17.173

Table 15.

Enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides.

graphic file with name Beilstein_J_Org_Chem-17-2585-i025.jpg

67 R1 R2 Ar Yield [%] ee [%]a

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.