Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
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(±)-<br />
NHAc<br />
Miller Peptide Catalyst - Round 2<br />
OH<br />
NHAc<br />
N<br />
N<br />
2 mol% Catalyst 8<br />
4.8 eq Ac 2 O<br />
PhCH 3 , 0 o C<br />
N<br />
Boc<br />
OH OH<br />
N<br />
H<br />
NHAc<br />
O<br />
O<br />
N<br />
H<br />
O<br />
Catalyst 8<br />
H<br />
N<br />
OMe<br />
O<br />
Bn<br />
OAc<br />
NHAc<br />
OH<br />
NHAc<br />
s = 28<br />
Miller has extended this hairpin turn structure to an octapeptide, which shows improved selectivities for<br />
this class of substrates:<br />
s = 51 s = 15 s = 27<br />
Miller, et. al., J. Am. Chem. Soc., 1999, 121, 11638<br />
10