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Additional info for Ab Initio Calculations: Methods and Applications in Chemistry
167,168 This reaction directly generates enantiomerically enriched N -Cbzprotected α-aryl amino esters, which are common intermediates for peptide synthesis. 169 The enantioselectivity, however, was in the moderate range. O N EDG OBn + CuPF6-(R)-Tol-BINAP (5-20 mol%) Cbz CH2Cl2 or THF, –78° EtO2C NH EDG (Eq. 58) EtO2C EDG = electron donating group 127 (44-88%) 52-98% ee Oxazole as a Glycine Enolate Equivalent. 170,171 Two catalytic enantioselective variants have been reported. First, the chiral nucleophilic pyridine derivative 128 catalyzed the enantioselective rearrangement of O-acylated azlactone 129 to α,α-disubstituted amino acid derivatives 130 with excellent enantioselectivity and broad substrate generality (Eq.
5 mL) was added slowly over 24 hours at −40◦ . A saturated aqueous solution of NaHCO3 was added after 40 hours, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with saturated NaCl and dried over Na2 SO4 . 0957. 015 mmol) was added at ambient temperature and the resulting solution was stirred for 1 hour. 5 mol% to trimethylaluminum) was then added and the mixture was stirred for 30 minutes. 7 mmol). After 48 hours, 5% aqueous NH3 was added. 1055. 5 mL). 01 mmol) was added and the mixture stirred at room temperature for 1 hour.
25 eq) was added. The solution was stirred for 2 hours at 5◦ , cooled to −78◦ , and then added to the reaction flask by syringe. When conversion of the starting material exceeded 99% as monitored by either 1 H NMR or HPLC, the solvents were removed under vacuum. The crude product was obtained as a solid (quantitative as a mixture with catalyst, 93% ee). 0414. 6 mmol) in THF (16 mL) at 4◦ , and the mixture was stirred at 50◦ for 1 hour. The solvent was evaporated, and the residue was dried under vacuum for 2 hours at room temperature.