Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
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Cl<br />
(±)-<br />
R 1<br />
R 1 = Ar<br />
OH<br />
R 2<br />
R 2 = Alkyl, CH 2 Cl<br />
DMAP Derivatives as Catalysts for Acylation - Fu<br />
OH<br />
Me<br />
1 mol% Catalyst 2<br />
Ac 2 O<br />
Et 3 N<br />
t-amyl alcohol<br />
0 o C<br />
Acetate can also be recovered in high ee<br />
R 1<br />
OH<br />
MeO<br />
R 2<br />
+<br />
50-55% conversion<br />
96-99% ee (alcohol)<br />
s = 32 - 95<br />
Catalyst is air/moisture stable and easily recoverable/reusable<br />
Resolution can be performed on large (2 g) scale<br />
Propargylic alcohols could be resolved, though generally with lower selectivities (s = 8 - 20)<br />
R 1<br />
OAc<br />
Me<br />
R 2<br />
OH<br />
Me<br />
O<br />
Et<br />
Me 2 N<br />
Ph<br />
Ph<br />
N<br />
Fe<br />
Ph<br />
Catalyst 2<br />
Allylic alcohols, especially cinnamyl alcohols, generally worked (s = 5.4 - 80), and were used to synthesize<br />
enantioenriched intermediates in several natural products:<br />
40% yield, 99.4% ee<br />
s = 37<br />
(-)-baclofen<br />
47% yield, 98.0% ee<br />
s = 107<br />
Ph<br />
Ph<br />
epothilone A<br />
Fu, et. al., J. Org. Chem., 1998, 63, 2794<br />
J. Am. Chem. Soc., 1999, 121, 5091<br />
Chem. Comm., 2000, 1009<br />
5
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