Chemistry Reference
In-Depth Information
TBSO
H
27
(10 mol %)
CHO
+
R
p
-Nitrophenol (20 mol %)
MeOH, r.t.
P
h
CHO
CHO
1)
Ph
3
P
CHCO
2
Et
+
R
R
2) Toluene, 120
°
C
R = Ph
CO
2
Et
R = Ph 92% ee (84%) 70:30
R =
p
-BrPh
95% ee (79%)
67:33
R =
p
-MeOPh 93% ee (82%) 57:43
endo
:
exo
>25:1
Scheme 8D.32.
28
:
Ar = 4-MeC
6
H
4
Ar
2
P
Cu
+
P
Ar
2
ClO
-
R
1
R
1
NTs
(5 mol %)
N
HTs
+
R
2
H
2
Et
BTF, r.t.
R
2
CO
2
Et
R
3
Ts
N
HTs
N
O
N
HTs
N
HTs
N
HTs
Ph
CO
2
Et
CO
2
Et
CO
2
Et
CO
2
Et
95% ee (85%)
99% ee (95%)
85% ee (90%)
90% ee (92%)
N
HTs
Ph
N
HTs
N
HTs
N
HTs
CO
2
Et
PhS
CO
2
Et
CO
2
Et
CO
2
Et
MeO
90% ee (91%)
98% ee (85%)
99% ee (94%)
94% ee (77%)
syn
/
anti
6/1
Scheme 8D.33.
of the enantioselective catalysis of imine-ene reaction untill 1998, because of the low
ene reactivity of glyoxylate-imines as compared with the parent glyoxylates.
Recently, Lectka et al. demonstrated the fi rst effective enantioselective imine-ene
reactions of readily available α - tosylimino ester with alkenes using Tol - BINAP - Cu(I)
(ClO
4
) complex
28
(Scheme 8D.33) [64]. A variety of aromatic, cyclic, and simple acyclic
