Table 2 Scope of the enantioselective R–C reaction catalyzed by poly(1s50-b-2100)a

From: Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water

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Run

R1/R2 (3)

R3 (4)

5

Yield (%)b

ee (%)c

1

4-F-C6H4/Et (3b)

CH3 (4a)

5ba

87

93

2

4-Cl-C6H4/Et (3c)

CH3 (4a)

5ca

90

94

3

4-Br-C6H4/Et (3d)

CH3 (4a)

5da

86

95

4

4-Me-C6H4/Et (3e)

CH3 (4a)

5ea

80

96

5

4-MeO-C6H4/Et (3f)

CH3 (4a)

5fa

84

95

6

4-Ph-C6H4/Et (3g)

CH3 (4a)

5ga

81

96

7

2-naphthyl/Et (3h)

CH3 (4a)

5ha

83

96

8

C6H5/Me (3i)

CH3 (4a)

5ia

85

95

9

C6H5/iPr (3j)

CH3 (4a)

5ja

83

95

10

C6H5/Bn (3k)

CH3 (4a)

5ka

82

96

11

4-Ph-C6H4/Et (3g)

4-Me-C6H4 (4b)

5gb

70

92

12

2-naphthyl/Et (3h)

4-Me-C6H4 (4b)

5hb

72

90

13

4-Ph-C6H4/Et (3g)

4-F-C6H4 (4c)

5gc

69

91

14

2-naphthyl/Et (3h)

4-F-C6H4 (4c)

5hc

70

90

15

2-naphthyl/Et (3h)

4-Cl-C6H4 (4d)

5hd

71

93

16

2-thienyl/Et (3l)

CH3 (4a)

5la

74

88

17

2-Furyl/Et (3m)

CH3 (4a)

5ma

76

84

18

tBu/Et (3n)

CH3 (4a)

5na

68

89

  1. aUnless otherwise specified, all reactions were carried out with 3 (0.1 mmol) and 4 (0.3 mmol) in water (5 mL, <5 volume % of THF were used in case the substrates could not be dissolved in water), and the catalyst loading was determined by elemental analysis.
  2. bYield of isolated products.
  3. cDetermined by HPLC analysis using a chiral column.
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