Chemistry Reference
In-Depth Information
CHO
R
4
R
2
R
2
Me
110
(20 mol %)
CH
2
Cl
2
/P
i
OH
-87 to -50
O
N
+
R
4
O
N
Bu
t
R
3
R
3
N
N
H
R
1
Bn
°
C
R
1
R
1
=H,Me,Bn,Allyl
110
Up to 94% yield
Up to 97% ee
R
2
=H,MeOMe
R
3
=H,Cl
R
4
=Me,Pr
n
,Pr
i
,Ph,CH
2
OBn, CO
2
Me
Scheme 8A.77.
136
promoted the alkylation of indoles with various aromatic and aliphatic nitroalkenes,
providing the desired 2-indolyl-1-nitro derivatives in good yields and enantioselectivities
(Scheme 8A.78 ) [150] .
R
2
CF
3
O
2
N
R
3
R
1
R
3
+
136
(20 mol %)
CH
2
Cl
2,
Î24
NO
2
R
2
S
H
°
C
R
1
F
3
C
H
H
R
1
=H,Me
R
2
=H,OMe,Cl
R
3
= Ph, 2-furyl, 2-thienyl, n-pentyl, Pr
i
H
OH
136
Up to 88% yield
Up to 89% ee
Scheme 8A.78.
F
3
C
R
*
+
R
NO
2
NH
NO
2
137
(10-20 mo
l %)
Me
N
H
S
CF
3
CDCl
3
F
3
C
S
HN
Me
R=Ph,4-CF
3
C
6
H
4
,4-BrC
6
H
4
,
2-MeC
6
H
4
, 2-thienyl, n-pentyl,
cyclohexyl
HN
Up to 98% yield
Up to 50% ee
CF
3
137
Scheme 8A.79.
Connon et al. [151] investigated and developed thiourea-based axially chiral organo-
catalysts and found that catalyst
137
afforded the corresponding alkylated products in
good yields (up to 98%) and moderate enantioselectivities (up to 50% ee) (Scheme
8A.79 ).
