Chemistry Reference
In-Depth Information
O
t
Bu
O
t
Bu
Me
3
OBF
4
HO
MeO
Proton Sponge™ (
1
)
O
O
CbzHN
4Å MS
CbzHN
O
O
O
CH
2
Cl
2
, rt
O
Me
Me
77%
Other conditions
NaH, MeI: 0%
LHMDS, Me
2
SO
4
: 0%
Ag
2
O, MeI: 0%
2,6-
tert
-butyl-4-methylpyridine, MeOTf: trace
CO
2
Me
CO
2
Me
N
N
Me
3
OBF
4
Proton Sponge™ (
1
)
H
H
H
H
4Å MS
SEMO
SEMO
OBn
OBn
CH
2
Cl
2
, rt
OMe
OH
97%
Other conditions:
n
BuLi, MeOTf: complex mixture
Effect of 4 A
molecular sieves on ether synthesis - II
Scheme 8.5
Me(CH
2
)
6
(CH
2
)
6
Me
NBSO
ONBS
TfO
(CH
2
)
6
Me
NBSO
ONBS
OH
HO
(a)
O
O
Proton Sponge™ (
1
)
O
O
CHCl
3
, 60 °C
O
O
14
14
83%
NBS: 3-nitrobenzenesulfonyl
TfO
Me
OH
8
6
O
Me
(b)
7
6
TBSO
OMPM
TBSO
OMPM
Proton Sponge™ (
1
)
CH
2
Cl
2
, reflux
66%
Scheme 8.6
O-Alkylation reaction with alkyl triflate in the presence of Proton Sponge (1)
