Table 1 Condition optimization.

From: Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis

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Entrya

NHC

Base

Solvent

Yield (%)b

ee (%)c

1d

A

K2CO3

DCM

nr

2e

A

K2CO3

DCM

nr

3

A

K2CO3

DCM

75

4

B

K2CO3

DCM

78

84

5

B

Cs2CO3

DCM

72

79

6

B

DBU

DCM

70

22

7

B

NaOAc

DCM

Trace

8

B

Et3N

DCM

Trace

9

B

DIPEA

DCM

Trace

10

B

DABCO

DCM

77

84

11

B

KHCO3

DCM

81

83

12

B

K3PO4

DCM

52

79

13

B

K2CO3

THF

Trace

14

B

K2CO3

DCE

63

87

15

B

K2CO3

CHCl3

75

69

16

B

K2CO3

1,4-Dioxane

Trace

17f

B

K2CO3

DCM

80

89

18g

B

K2CO3

DCM

89

93

19h

B

K2CO3

DCM

85

95

20h,i

B

K2CO3

DCM

82

93

21h,j

B

K2CO3

DCM

80

92

22h

C

K2CO3

DCM

84

9

23h

K2CO3

DCM

nr

  1. nr no reaction.
  2. aStandard condition: 1c (0.1 mmol), 2a (1.5 equiv.), NHC precursor (20 mol %), base (1.5 equiv.), solvent (0.1 M), 30 °C, N2, 12–72 h.
  3. bYield (after SiO2 chromatography purification) were based on 1a.
  4. cDetermined via chiral phase HPLC analysis.
  5. d1a was used.
  6. e1b was used.
  7. f0 °C.
  8. g−20 °C.
  9. h−30 °C.
  10. iNHC precursor (15 mol %).
  11. jNHC precursor (10 mol %).