Chemistry Reference
In-Depth Information
-
+
+
Bn
Ph
CO
2
t
Bu
N
CO
2
t
Bu
N
base
ArCHO
NMe
MeN
NMe
Br
-
MeN
base
HBr
L
L
L
L
23
22
t
BuO
2
C
Ar
O
BnN
SiO
2
O
NMe
MeN
NMe
MeN
L
L
26
CO
2
t
Bu
L
L
Bn
L = H or Ph
N
24
Ar
Bn = CH
2
Ph
25
Selected data for asymmetric aziridination with
22
(L = Ph) in the presence of TMG (
1
) as a base
yield (%) of
25
de
(%)
time
(h)
run
Ar
22
cis
(ee)
trans
(ee)
total
O
1
4
82 (97)
(
R,R
)
6
88
86
O
MeO
2
4
73 (84)
(
S,S
)
8
81
80
MeO
3
4
12
39
51
53
(
S,S
)
N
4
7
6
70 (95)
76
84
(
S,S
)
N
Boc
5
5.5
(
S,S
)
9
87 (76)
96
82
Boc
Scheme 4.39 New synthesis of aziridine 25 from guanidinium salt 22 and aryl aldehydes
through spiro intermediates under basic conditions
