Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
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(±)-<br />
(±)-<br />
Et 3N<br />
Me<br />
(±)-<br />
Ph<br />
Ph<br />
OH<br />
n<br />
N<br />
H<br />
OH<br />
OH<br />
OH<br />
Proposed Oriyama Diamine Mechanism<br />
Et 3NHCl<br />
Cl -<br />
N R1<br />
R 2<br />
OH<br />
R<br />
R 1<br />
OBz<br />
n<br />
R 2<br />
N<br />
Me<br />
R 1<br />
N<br />
R 2<br />
R 1<br />
OH<br />
R 2<br />
Me<br />
Phosphines as Catalysts - Vedejs<br />
5-8 mol% Catalyst 5<br />
Ph<br />
Ph<br />
(R'CO) 2 O<br />
CH 2 Cl 2 , r.t.<br />
OH<br />
OAc<br />
OCOR'<br />
OH<br />
n = 1, s = 3.2<br />
n = 2, s = 4.3-5.1<br />
R' = CH 3, s = 1.2<br />
R' = Ph, s = 5.5<br />
OH<br />
R<br />
+<br />
N<br />
Ph<br />
O<br />
BzCl<br />
Cl -<br />
N R1<br />
R 2<br />
Oriyama, et. al. Synthesis, 1999, 1141<br />
OCOR'<br />
R<br />
R = CH 3 , R' = CH 3 , s = 2.7<br />
R = CH 3 , R' = m-Cl-Ph, s = 2.8<br />
R = t-Bu, R' = CH 3, s = 3.8<br />
R = t-Bu, R' = m-Cl-Ph, s = 12-15<br />
(10 days at room temp)<br />
Me<br />
P Ph<br />
Me<br />
Catalyst 5<br />
Vedejs, J. Org. Chem. 1996, 61, 430<br />
7
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