Chemistry Reference
In-Depth Information
TABLE 10.10. Iodine(III)-Mediated, Cyclization of N-p-Methoxyphenyl-Substituted
4-Pentenamides via Alkene Trifluoroacetoxyamidation
O
PIFA
BH
3
Ar
O
H
N
Ar
N
Ar
HO
HO
568
569
570
Yield (%)
a
Entry
Substrate
Product
1
70 (R
¼
ph), 83 (R
¼
1-Naph)
O
570a
570b
Ar
N
Ar
H
HO
568
2
42 (dr
¼
5.6:1)
O
t
-Bu
t
-Bu
PMP
H
570c
N
PMP
568c
HO
3
52 (dr
¼
2.3:1)
O
Me
PMP
H
570d
N
PMP
Me
568d
HO
4
74
O
Me
570e
PMP
N
PMP
H
HO
568e
Me
5
12
O
H
PMP
H
570f
N
H
HO
PMP
568f
6
-
O
PMP
H
Complex mixture
Me
568g
76
b
7
O
O
PMP
PMP
Me
H
Me
H
Me
Me
568h
571h
a
Over two steps.
b
Reduction step omitted.
