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Ph
O
CF 3
OO
107
O
F 3 C
O
F 3 C
CF 3
O
NO 2
101 (10 mol %)
NO 2
93->98% de, 60-89% ee
50-88% yield
Ar
Ph
R
Toluene
60A
108
R = aryl
OH
109
R '
NO 2
NO 2
R '
R
85-94% ee
69-83% yield
OH
101 (10 mol %)
60
R = aryl, alkyl
Toluene, -50°C
4ÅMS,96h
R '
110
HO
N
111
EtO 2 C
NO 2
CO 2 Et
N
89-93% ee
68-83% yield
R
O
*
103 (10 mol %)
60B
NO 2
R
R = alkyl
Toluene, -24°C
112
N
N
N
F 3 C
H
OMe
O
CF 3
N
115
S
OH
O
O
MeO
113
NO 2
S
R
NO 2
115 (10 mol %)
60B
O
R
MeO
R = alkyl
Toluene, -24°C
73-90% ee
13-97% yield
114
Scheme 2B.23.
decarboxylative Michael addition of β - ketoacid 113 reported by Wennemers and
coworkers [64] presented a successful organocatalytic approach toward synthetically
valuable asymmetric transformations that were previously only successful with chiral
metal catalysts [65] .
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