Table 1 Summary of key reaction parameter effectsa

From: Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide

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Entry

Deviation from standard conditions

Yield (%)b

e.e. (%)c

1

None

97

97

2

(S)-4b

77

93

3

(S)-4c

56

81

4

(S)-4d

89

95

5

(S)-4e

37

20

6

(S)-4f

57

67

7

(S)-4g

62

66

8

without MgSO4

53

97

9

Na2SO4 instead of MgSO4

45

81

10

4 Å MS instead of MgSO4

trace

ND

11

CHP instead of H2O2

16

93

12

TBHP instead of H2O2

27

97

13d

CH2Cl2 instead of Toluene

96

97

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  1. aStandard reaction conditions using 1aa (0.1 mmol), 2 (0.2 mmol), MgSO4 (120 mg), and (S)−4a (3 mol %) at 35 oC for 5 h in toluene (1.0 mL) unless otherwise noted. bIsolated yields. cEnantiomeric excess (e.e.) and diastereomeric ratio (d.r.) values were determined using chiral HPLC analysis or 1H NMR analysis (GC). d18 h. MS molecular sieves; CHP cumene hydroperoxide; TBHP tert-butyl hydroperoxide; ND not detected.