org.rxn.mech15b

org.rxn.mech15b, Podrecznik - Mechanizmy Reakcji

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# 1
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3
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OMe
OMIP
OMIP
CHO
heat
N
3
N
3
OMe
N
N
OMe
MIP = 2-methoxyisopropyl
N
h
ν
OMIP
OMIP
OMIP
H
2
O
N
O
N
OMe
N
OMe
H
S
CHEME
67
('!
O
O
O
O
O
2
OOH
+
OOH
OH
OH
HO
OH
HO
OH
HO
HO
OH
(
298
)
OH
(
299
)
S
CHEME
68
#
'
&
'
/
44
+ 3
/ !
! #
R
1
NR
2
R
3
NR
2
R
3
Cl
SiMe
3
PC
PC
+
R
1
P
C
Cl
P
CH
2
SiMe
3
Me
CH(SiMe
3
)
2
(
300
)
(
301
)
(
302
)
R
1
NR
2
R
3
R
1
NR
2
R
3
+
P
C
P
PC
C
P
CH
H
(Me
3
Si)
2
CH
(Me
3
Si)
2
CH
H
(
303
)
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+ 5 +# 6
/
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+ 5
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# 7 +
/ +
#
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3
3
/ 8
',
#
'.
#
NTs
Pd(dba)
2
PPh
3
AcOH
NTs
(
E
)
(
Z
)
AcO
Ph
H
HPh
(
305
)
(
304
)
& 9
279
#
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&
+
("
/
:;& - *0# '( +
(* ' ! +
(!
! ! -%
<=
-%& ( / ! *
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/ '
/ ( ! ' #
(
OR
OSiMe
3
Me
Me
Me
OSiMe
3
LA
R′
+
SO
2
Me
OR
Me
OR
H
R′
SO
SO
2
–
LA
Me
O
LA = Lewis acid
(
306
)
(
307
)
R = SiMe
2
Bu
t
O
Me
Me
Me
O
OR
O
Me
S
Me
3
SiO
2
S
R′
–
O
H
OR
H
Me
H
OR
R′
R
′
O
Me
(
309
)
(
308
)
('
Br
SH
S
FVT
n
-BuLi
H
S
CHEME
69
& >!? @
(
#
('
A >!? @
((
@ +
- ," #
(*
& @
/
(,
#
6 "
# >!?
/
(.
# 7
R
2
R
1
R
2
Si
O
H
R
3
R
1
H
R
SiR
1
R
2
R
3
R
Pd(0
)
Si
R
3
R
O
H
H
+
PdL
2
–
O
(
310
)
H
H
(
311
)
(
312
)
>!? >!(?
#
(0
>!?
*"
B 6;
/ @ #
*!
/ !
</ - ,!#
& >!*? </
NOMe H
NOMe Li
NOMe
LDA
R
R
R
R
OR
OR
S
CHEME
70
OH
(''
(i) Bu
t
Li
O
TBSO
S
S
OH
(ii)
BnO
S
S
BnO
OTBS
(iii)
O
OTBS, HMPA
TBS
S
CHEME
71
>!? </
*
!
' ! ( -
,# 6
*
1
-2 <
=
-2 % 2
=
- - ,# & >!'? </
*'*(
>!'? </
! #
**
+
+
O
O
–
O
SiMe
3
TMS
TMS
–
OBn
OBn
OBn
SiMe
3
SiMe
3
Me
3
Si
–
O
O
O
re
tro-Brook
–
–
OBn
OBn
OBn
H
+
CHO
BnO
SiMe
3
S
CHEME
72
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