Table 2 Optimizations for intramolecular hydrosilylation

From: Iron-catalyzed sequential hydrosilylation

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Entry

Catalyst

x

Base

Solvent

Time (h)

Yieldb (%)

ee of 8ac (%)

1a

Fe-1

5

NaOtBu

THF

12

60

58

2

Fe-6

5

NaOtBu

THF

12

62

60

3

Fe-7

5

NaOtBu

THF

12

66

61

4

Fe-8

5

NaOtBu

THF

12

62 (83:17 rr)

75

5

Fe-8

5

NaBHEt3

THF

12

90

74

6

Fe-8

5

NaBHEt3

Neat

12

95

79

7

Fe-5

5

NaBHEt3

Neat

12

73

90

8

Fe-5

2

NaBHEt3

Neat

12

90

90

9

Fe-5

2

NaBHEt3

Neat

3

91

91

10

Fe-9

2

NaBHEt3

Neat

3

90

87

  1. aStandard conditions: 7a (0.50 mmol), cat. Fe (0.025 mol), NaOtBu (0.075 mmol), THF (1 mL).
  2. bYields were determined by 1H NMR using TMSPh as an internal standard.
  3. cThe enantiomeric excess ratio (ee) was determined by chiral HPLC.
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