Chemistry Reference
In-Depth Information
OSiMe
3
SO
2
Ph
1.
SO
2
Ph
2. Ce(NH
4
)
2
(NO
3
)
6
Fe(CO)
4
O
9.27
9.25
SO
2
Ph
1.
n
-BuLi
2. furfural
3. (COCl)
2
, DMSO, Et
3
N
1. H
2
, Pd/C
2.(CH
2
OSiMe
3
)
2
O
O
9.28
O
O
Zn, AcOH
O
SO
2
Ph
O
O
O
9.30
9.29
O
Scheme 9.9
Fe
(CO)
4
Fe(CO)
4
Fe
2
(CO)
9
3 : 1
+
O
O
i
-PrO
i
-PrO
O
i
-PrO
N
Ac
N
Ac
N
Ac
9.31
9
3
9
3
SiMe
3
18 hrs
3 hrs
BF
3.
OEt
2
Fe(
CO)
4
F
e
(
CO)
4
O
O
N
Ac
N
Ac
9
9
O
O
N
Ac
N
Ac
9.36
55% e.e.
9.37
> 95% e.e.
Scheme 9.10
reacts slowly to give the product
9.36
with inversion but low e.e. (Scheme 9.10). This is because the leaving
group and the iron are
cis
, an unfavourable arrangement for ionization.
9.2 Catalysis: Mostly Palladium
-Allyl palladium
9.39
complexes can be made directly from alkenes in a process that involves C-H activation
(Scheme 9.11 - see Section 3.4), though they are more often made from allyl halides by treatment with a
source of palladium(0) (Scheme 9.12). They are stable, isolable compounds, usually existing as dimers with
