Chemistry Reference
In-Depth Information
O
NHAc
Ar
HN
ent
-PA
1i
(10 mol %)
R
1
R
1
Ar
H
Toluene, 4A MS
H
14 examples
94-99% yield
73-97% ee
O
X
N
O
H
O
O
P
O
H
N
X
TS 4
Scheme 3.33.
NHR''
R
R''
N
ent
-PA
1h
(10 mol %)
R'
R
N
H
N
H
Toluene, -60°C
R'
19 examples
68-93% yield
82-99% ee
Scheme 3.34.
C
O
2
Et
CO
2
Et
R
EtO
2
C
CO
2
Et
O
NH
2
e
nt
-PA
1h
(20 mol %
)
R
NH
R
1
H
H
H
Na
2
SO
4
Toluene, -30°C
R
1
20 examples
40-98% yield
62-96% ee
Scheme 3.35.
Terada and others reported the quite interesting alkylation of
α
- diazoesters with
N
-
acyl imines to afford
-diazoesters in high yields and enantioselectivities [63].
Diazoacetate is commonly employed in aziridine formation reactions under Lewis acidic
and Brønsted acidic conditions (aza-Darzene reaction). Earlier, Williams and Johnston
observed that Brønsted acids, such as TfOH, catalyzed aziridine formation from diazo-
acetate and
N
-benzyl imines [64]. After carefully considering the reaction mechanism
β
- amino
α
