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. Author manuscript; available in PMC: 2020 Feb 13.
Published in final edited form as: J Am Chem Soc. 2019 Jan 30;141(6):2645–2651. doi: 10.1021/jacs.8b13006

Table 3.

Optimization of Enantioselective Oxidative Dearomatizationa

graphic file with name nihms-1010151-t0019.jpg
entry cat. mol % [O] T (°C) era yield (%)b
 1 CN-1 20 H2O2 (aq)   0 55:45  <10
 2 CN-2 20 H2O2 (aq)   0 50:50  <10
 3 CN-3 20 H2O2 (aq)   0 63:37  <10
 4 CN-3 20 UHP   0 69:31   33
 5 QN-1 20 UHP   0 85:15   50
 6 QN-1 20 UHP  −10 87:13   55
 7 QN-1 20 UHP  −20 80:20   43
 8 DHQ-1 20 UHP  −10 87:13   52
 9 QN-2 20 UHP  −10 85:13   70
 10 QN-2 20 UHP  −40 87:13   85
 11 QN-2 10 UHP  −40 87:13   86
graphic file with name nihms-1010151-t0020.jpg
a

Reactions were performed using 8a (0.50 mmol), KOH (1.5 mmol), UHP (1.5 mmol), and [8a]0 = 0.05 M in CH2Cl2. 8a was added over the course of 2.5 h.

b

er was determined by chiral HPLC.

c

Isolated yields.