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H H
*
bonds formed by Navarov reactions
*
carbon atoms derived from CO
*
H
4.25
O
Me 3 Sn
(Ph 3 P) 4 Pd,
LiCl, CO
OTf
BF 3 .OEt 2
+
SiMe 3
SiMe 3
4.26
4.27
4.28
Me 3 Sn
O
(Ph 3 P) 4 Pd,
LiCl, CO
H
OTf
1. H 2 , Pd/C
2. LDA, Tf 2 NP h
H
4.27
SiMe 3
4.29
4.30
O
O
H
1. BF 3 .OEt 2
2. H 2 , Pd/C
H
H
H H
Ph 3 P
CH 2
SiMe 3
H
H
4.31
4.32
4.25
Scheme 4.13
n -C 6 H 13
O
O
n -C 6 H 13
double
aza-Michael
NH 2
H
N
OPG
OH
4.33
4.34
OTf
carbonylative
coupling
R
n -C 6 H 13
CO
M
4.35
4.36
O
n -C 6 H 13
1. (MeCN) 2 PdCl 2 , aq. MeOH
2. TBSCl, Et 3 N, DMAP
3. MsCl, Et 3 N
4. NaN 3 , DMF
OTf
n -C 6 H 13
Me 3 Sn
(Ph 3 P) 4 Pd, LiCl
THF, CO, Δ
O
O
O
O
4.35
4.37
n -C 6 H 13
O
n -C 6 H 13
O
N 3
1. CrCl 2 , H 3 O +
2. TBAF
H
N
OTBS
OH
4.38
4.33
Scheme 4.14
 
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