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Cours Hanoi RG Synth Asym Part 2
Cours Hanoi RG Synth Asym Part 2
A B
A
R2 R2
C Z C*
R1 R1
Z B
Enantiomers
Z B
R2 R2
C Z C*
R1 R1
A
A B
General principles on stoichiometric asymmetric synthesis
A B *
* - X
X A A
R2 R2
R2 R2 C* C*
C Z C Z R1 R1
R1 R1 Z B Z B
* *
X X
Major
*
* - X
X Z B
R2 Z B
R2 R2 R2
C Z C* C*
C Z R1
R1 R1 A R1
A
* *
X A B X
*
Minor X : Chiral auxiliary (temporay)
Note: extension to asymmetric catalysis
Reaction on the
upper face favored
A B
Coordination very important
R2
C Z
R1
organometallic catalyst
or enzyme
A B
Re face
O
Nu O- Nu-
1 Nu- -
3 O Nu
R 2 H
R * H Si face Re face R * H
attack attack
Si face
Li+ Re face
R'O O-
1 R"-X
R" CO2R' R"-X R'O2C R"
3
R 2 H
R * H R
Si face Re face * H
attack attack
Si face
1st pathway: chirality on substrate
New chiral
centre
created
Chirality *
on
substrate
2nd pathway: chirality on reagent
Chirality
on reagent
Temporary
chiral
auxiliary
Recycled Auxiliary
Conclusions and important points