Table 1 Optimization of the reaction conditionsa

From: Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles

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Entry

L

“N3

Solvent

Time (h)

Yield (%)

ee (%)

1

L1

1a

DCE

24

35

14

2

L2

1a

DCE

24

28

12

3

L3

1a

DCE

24

50

23

4

L4

1a

DCE

24

37

75

5

L5

1a

DCE

24

44

44

6

L6

1a

DCE

24

40

82

7

L7

1a

DCE

24

45

80

8

L8

1a

DCE

24

62

92

9

L9

1a

DCE

24

47

33

10

L10

1a

DCE

24

52

31

11

L8

1a

DCM

24

70

94

12b

L8

1b

DCM

24

30

27

13c

L8

1c

DCM

48

80

90

14c

L8

1d

DCM

48

99

94

15c

L8

1e

DCM

48

78

94

16c

L8

1f

DCM

48

95

93

17c

L8

1g

DCM

48

93

93

  1. DCE: 1,2-dichloroethane, DCM: dichloromethane, L: Ligand; N3: high iodine azide reagent; 1a: azidobenziodoxolone, 1b: azidodimethylbenziodoxole; 1cg: azidobenziodazolones.
  2. aReaction conditions: 2a (0.1 mmol), 1a (0.15 mmol), Cu(MeCN)4PF6 (10 mol%), L (12 mol %), solvent (2 mL), 25 °C; isolated yields; ee values were determined by HPLC analysis.
  3. b1b was used in place of 1a.
  4. cThe designated azidating reagent was used in place of 1a; 5 mol % of Cu(MeCN)4PF6 and 6 mol% of L8 were used instead.