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Felkin-Anh. Anti-Cram or. Cram Chelate. S = Small. M = Medium. L = Large. The Felkin Anh Model. Chem. Rev. 1999, 99, 1199. Page 2. The Cram Chelate Model.
Typology: Lecture notes
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Entry FA : CC
M Nu
Ph 19 17 : 83
p - Tol
Ph 20 02 : 98
Ph 21 04 : 96
p - Tol
Ph 22 12 : 88
Ph
Ph 23 34 : 66
Ph
NBn
2
Me
13 95 : 05
NBn
2
Me
14 06 : 94
Ph
SMe
Et
15
Li(
s
Bu)
3
Ph
2
Me
Me
17 73 : 27
Ph
Me
18 03 : 97
Ph
SMe
Et
16 06 : 94
Ph
H LiAlH
4
H PhMgBr
H CH PhMgBr
3
3
PhLi
3
MeMgBr OH
3
H H MgBr
3
TiCl
3
3
H NaBH
4
NHAc
4
2
Me
Zn(BH
4
2
Zn(BH
4
2
Nu
Nu
Felkin-product anti - Felkin-product
nucleophile
2
nucleophile FA:CC
allylMgBr 60:
allylTi(O
i
Pr) 3
(allyl) 2
Zn 90:
PhLi 48:
PhMgBr 48:
PhTi(O
i
Pr) 3
MeLi 60:
MeMgBr 67:
n
BuLi 69:
n
BuMgBr 75:
i
BuMgBr 75:
n
BuTi(O
i
Pr)
3
Li
Li
Li CH(OEt)
2 70:
S S
Ph Li , Ti(O
i
Pr)
4
S S
Ph Li
, Zr(O
i
Pr) 4
S S
Ph Li
, ZnBr 2
S S
Ph Li
, MgBr 2
B(O
i
Pr)
2