Chemistry Reference
In-Depth Information
AcO
AcO
1. Et
3
SiH, BF
3
OEt
2
2. NH
3
1. AcCl
2. NH
2
CH
2
CH
2
CN
HO
1. NaBH
4
, MeOH
O
O
O
AcO
N
N
HO
2
C
2
H
3. Ac
2
O
2. Ac
2
O, Et
3
N
cat. DMAP
3. Th(CH
3
)
2
SiCl
63%
CN
CN
76%
Th(H
3
C)
2
SiO
Th(H
3
C)
2
SiO
1. NaBH
4
CoCl
2
MeOH, NH
3
Th(H
3
C)
2
SiO
MeI
S
O
SMe
N
N
N
2. (Boc)
2
O
1. TFA
NHBoc
CN
3. Lawesson reagent
NHBoc
2. NaOH
53%
Th =C(Me)
2
CHMe
2
Th(H
3
C)
2
SiO
Th(H
3
C)
2
SiO
NN
N
N
N
NH
Scheme 3.15
Synthesis of bicyclic amidine from (S)-malic acid via thioimidate
