Kinetic Resolutions - The Stoltz Group

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OH (±)- Nucleophilic Catalysts for Acylation - Oriyama R 1 OH R 2 N Me OH 0.3 mol% Diamine Catalyst 3 or 4 BzCl, Et 3N, CH 2Cl 2 MS4A, -78 o C, 3 hr Me N Catalysts: Bn N R 1 R n = 1, 2, 4 s = 4 R = H, s = 9 R = Ph, CO2Et, CO2i-Pr, Br R = Me, s = 20 n s = 27 (esters) to 170 R OH R 2 3 Me 4 N + Ph O R 1 O R 2 OH Oriyama, et. al., Chem. Lett. 1999, 265 6
(±)- (±)- Et 3N Me (±)- Ph Ph OH n N H OH OH OH Proposed Oriyama Diamine Mechanism Et 3NHCl Cl - N R1 R 2 OH R R 1 OBz n R 2 N Me R 1 N R 2 R 1 OH R 2 Me Phosphines as Catalysts - Vedejs 5-8 mol% Catalyst 5 Ph Ph (R'CO) 2 O CH 2 Cl 2 , r.t. OH OAc OCOR' OH n = 1, s = 3.2 n = 2, s = 4.3-5.1 R' = CH 3, s = 1.2 R' = Ph, s = 5.5 OH R + N Ph O BzCl Cl - N R1 R 2 Oriyama, et. al. Synthesis, 1999, 1141 OCOR' R R = CH 3 , R' = CH 3 , s = 2.7 R = CH 3 , R' = m-Cl-Ph, s = 2.8 R = t-Bu, R' = CH 3, s = 3.8 R = t-Bu, R' = m-Cl-Ph, s = 12-15 (10 days at room temp) Me P Ph Me Catalyst 5 Vedejs, J. Org. Chem. 1996, 61, 430 7
Page 1 and 2: N Me N Kinetic Resolutions Episode
Page 3 and 4: (±)- Evans - Oxazolidinone Acylati
Page 5: Cl (±)- R 1 R 1 = Ar OH R 2 R 2 =
Page 9 and 10: BocHN (±)- N N Tripeptides for Acy
Page 11 and 12: CO2R PPh3 N N RO2C RO2C CO2R HN NH
Page 13 and 14: Nishiyama, Sekar (our very own!) n
Page 15 and 16: t-Bu R 3 OH R 1 R 1 R 1 (±)- + + R
Page 17 and 18: (±)- Gardiner (±)- (±)- MeO 2C P
Page 19 and 20: Sharpless Et t-Bu Proposed Asymmetr
Page 21: R (CH2)3CH3 CH 3 (CH2)11CH3 (CH 2 )

Kinetic Resolutions - The Stoltz Group

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