Table 1 Evaluation of chiral ligands

From: Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

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Entry

Ligand

Conv. (%)

Yield (%)

2a/3a

ee (%)

2a+3a

4a

1

L1

98

96

2

>99

92

2

L2

>99

>99

0

>99

42

3

L3

99

99

0

>99

48

4

L4

>99

>99

0

>99

80

5

L5

94

94

0

>99

60

6

L6

44

29

15

>99

−9

  1. Reaction conditions: 1a (0.5 mmol), Rh(acac)(CO)2 (0.5 mol%), ligand (1.0 mol%), CO (10 bar), H2 (10 bar), toluene (2 ml), 70 °C, 20 h. Conversions and yields were determined by 1H NMR analysis. Enantiomeric excesses (ee) were determined by HPLC analysis using a chiral stationary phase after NaBH4 reduction