Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
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(±)-<br />
R 1<br />
OH<br />
n<br />
n<br />
R 1<br />
R 2<br />
OCOR<br />
OH<br />
NHR<br />
OH<br />
5 mol% Catalyst 1<br />
(i-PrCO) 2O, r.t.<br />
OH<br />
OH<br />
OCOR<br />
R = i-Pr, t-Bu, Ph, p-NMe 2C 6H 4CO-<br />
NHR<br />
R = p-NMe 2C 6H 4CO-<br />
R 1<br />
Only anti- acyclic substrates were selective<br />
Acylation with DMAP Derivatives - Fuji<br />
OH<br />
R 1<br />
R 2<br />
OCOR<br />
OH<br />
NHR<br />
OH<br />
+<br />
R 1<br />
2-5 hours<br />
R 1<br />
~70% conv.<br />
54-99% ee<br />
R 2<br />
s = 2.4 to > 10.1<br />
9-44 hours<br />
58-73% conv.<br />
89-99% ee<br />
s = 10 to > 18<br />
OCOi-Pr<br />
H H<br />
N<br />
Me 2N<br />
H<br />
OH<br />
R<br />
N<br />
R<br />
OH 2-naphthyl<br />
H<br />
Catalyst 1<br />
N<br />
NH<br />
O<br />
N<br />
OH<br />
O<br />
Cl -<br />
Fuji, et. al. J. Am. Chem. Soc., 1997, 119, 3169<br />
Chem. Comm., 2001, 2700<br />
4
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