Table 1 Initial studies and reaction optimizationa

From: Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles

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Entry

NHC

base

solvent

yield (%)b

erc

1

A

Na2CO3

THF

40

96:4

2

B

Na2CO3

THF

10

90:10

3

C

Na2CO3

THF

N.R.

–

4

A

Et3N

THF

42

99:1

5

A

K2CO3

THF

51

97:3

6

A

NaOAc

THF

32

98:2

7

A

K2CO3

EA

56

96:4

8

A

K2CO3

DCE

N.R.

–

9

A

K2CO3

DMSO

N.R.

–

10

A

K2CO3

NMP

N.R.

–

11

A

K2CO3

MTBE

N.R.

–

12

A

K2CO3

MeCN

66

98:2

13d

A

K2CO3

MeCN

63

98:2

14e

A

K2CO3

MeCN

61

98:2

  1. aUnless otherwise specified, the reactions were conducted with 1a (0.13 mmol), 2a (0.10 mmol), NHC (0.02 mmol), base (0.02 mmol), DQ A (0.13 mmol), 4 Å MS (150 mg) and solvent (2.0 mL) at 45 °C for 12 h.
  2. bIsolated yield of 3a.
  3. cThe er values were determined via HPLC on chiral stationary phase.
  4. dThe reaction uses DQ B as the oxidant.
  5. eThe reaction uses BQ as the oxidant.