Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
Kinetic Resolutions - The Stoltz Group
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R<br />
(CH2)3CH3<br />
CH 3<br />
(CH2)11CH3<br />
(CH 2 ) 2 CH=CH 2<br />
CH 2Ph<br />
c-C 6H 11<br />
t-Bu<br />
CH2Cl<br />
CH 2 F<br />
CF 3<br />
CH 2OBn<br />
CH 2OTBS<br />
CH2OPh<br />
CH 2 O(1-naphthyl)<br />
Resolution Through Epoxide Hydrolysis - Jacobsen<br />
(±)-<br />
R<br />
Epoxide<br />
% Yield<br />
(>99% ee)<br />
43<br />
46<br />
43<br />
43<br />
46<br />
44<br />
41<br />
43<br />
43<br />
43<br />
48<br />
47<br />
47<br />
38<br />
O<br />
R<br />
oxiranyl<br />
0.2-0.85 mol% 20<br />
0.55 eq H 2 O<br />
5-68 hr, r.t.<br />
CH 2 OCO(CH 2 ) 2 CH 3<br />
CH2CO2Et<br />
CO 2 Me<br />
COMe<br />
COEt<br />
CH=CH 2<br />
Ph<br />
(p-Cl)C 6 H 4<br />
(m-Cl)C 6 H 4<br />
(o-Cl)C6H4<br />
(m-OMe)C 6 H 4<br />
(m-NO2)C6H4<br />
TBS<br />
R<br />
Epoxide<br />
% Yield<br />
(>99% ee)<br />
Other <strong>Kinetic</strong> <strong>Resolutions</strong><br />
36<br />
46<br />
43<br />
43<br />
40<br />
41<br />
36<br />
44<br />
39<br />
40<br />
38<br />
41<br />
37<br />
41<br />
O<br />
+<br />
R<br />
OH<br />
OH<br />
N N<br />
Co<br />
t-Bu O O<br />
t-Bu<br />
t-Bu<br />
(R,R)-20<br />
t-Bu<br />
- OAc + H2 O<br />
Jacobsen, et. al., Science, 1997, 277, 936<br />
Beta-hydroxy amine resolution through N-oxide formation: Sharpless, J. Org. Chem., 1983, 48, 3608<br />
Epoxide to Allylic Alcohol Resolution: Andersson, Org. Lett., 2002, 4, 3777 and J. Am. Chem. Soc., 2000, 122, 6610<br />
Also, Feringa, Org. Lett., 2000, 2, 933<br />
Alpha-amino acid N-carboxyanhydrides to alpha-aryl amino acids: Deng, Org. Lett., 2002, 4, 3321<br />
Alpha-hydroxy epoxide resolution through semipinacol rearrangement: Tu, Tet. Asym., 2002, 13, 395<br />
Meso-diol desymmetrization through Dioxane acetal ring cleavage: Harada, J. Org. Chem., 2002, 67, 7080<br />
Dynamic <strong>Kinetic</strong> Resolution of alpha-halo acids to beta-amino alcohols: Durst, J. Org. Chem., 1998, 63, 3117<br />
Oxidative Sulfoxide: Uemura, J. Org. Chem., 1993, 58, 4529<br />
Baeyer-Villiger: (review) Bolm, Beckmann, Comprehensive Asymmetric Catalysis Vol II , Springer, NY, 1999, Ch. 22<br />
Carboxylic Acid Acylation: Najera, Tet. Asym., 1992, 3(11), 1455<br />
!-Allyl Pd - Many examples: Reetz, J. Organomet. Chem., 2000, 603, 105; Trost, JACS, 1999, 121, 3543<br />
Also, Gais, J. Am. Chem. Soc., 2003, 125 6066; Osborn, ACIEE, 1998, 37, 3118<br />
Metal-Mediated Cross-Coupling (Heck, MgR Coupling, etc.): Lloyd-Jones, Tetrahedron, 1998, 54, 901<br />
Also, Hayashi, J. Am. Chem. Soc., 1995, 117, 9101; Shibasaki, Tet. Lett., 1999, 40, 311<br />
Aziridine Carbonylation: Alper, J. Am. Chem. Soc., 1989, 111, 931<br />
Diazocyclization: Doyle, Russ. Chem. Bull., 1995, 44, 1729<br />
Anhydride Opening: Deng, J. Am. Chem. Soc., 2001, 123, 11302<br />
Ring-Closing Metathesis: Grubbs (of course!), J. Am. Chem. Soc., 1996, 118, 2499, and J. Org. Chem., 1998, 63, 824<br />
Also, Hoveyda and Schrock, J. Am. Chem. Soc., 1998, 120, 4041<br />
Cyclic Allylic Ether Resolution through Zr catalyzed MgR addition: Hoveyda, J. Org. Chem., 1999, 64, 9690<br />
Horner-Emmons-Wadsworth: Rein, Angew. Chem., Int. Ed. Engl., 1994, 33, 556<br />
Imine Resolution: Buchwald, J. Org. Chem., 2000, 65, 767<br />
Intramolecular Rh-catalyzed alkynyl ketone cyclization KR: Fu, J. Am. Chem. Soc., 2002, 124, 10296<br />
21
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