Kinetic Resolutions - The Stoltz Group

(±)-ROH +
O
EtO 2 C
O
N
H
HO 2C O
O
PPh 3
N
CO 2 Et
ROH
More Mitsunobu KR - Chandrasekhar
PPh 3 , DEAD
CH 2 Cl 2 , -23 o C
O
O
RO
O
PPh3
(-)-ROH +
KOH
EtOH
(-)-ROH +
RO2C O
ROH = Arylalkylalcohol, (-)-ROH from Mitsunobu: ~40% yield, 70-90% ee
(-)-ROH after saponification: ~80% yield, ~80% ee
M
O
L
H
O
O
O
PPh 3
HO 2C O
RO 2 C
Chandrasekhar, Kulkarni, Tet. Asym., 2002, 13, 615
O
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