Table 2 Analysis of the asymmetric hydrogenation of N-methyl-1-phenylethan-1-imine

From: Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures

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Entry

Reaction conditions

Traditional analysisa

Chiroptical sensingb

Ligand

Cat. load. (mol%)

Time (h)

Abs. config.

% ee

Conv.

Abs. Config.

% ee

Conv.

1

49

5.00

18

S

55.8

99.9

S

59.8

96.0

2

50

5.00

18

R

16.3

99.9

R

14.3

99.9

3

51

5.00

18

R

31.0

99.9

R

32.2

99.1

4

52

5.00

18

R

31.4

99.9

R

25.8

98.0

5

53

5.00

18

S

16.3

92.0

S

14.2

96.3

6

49

2.50

1

S

46.2

51.1

S

47.8

53.9

7

49

3.25

1

S

57.3

63.3

S

54.5

68.4

  1. aThe enantiomeric excess and conversion were determined by chiral HPLC and 1H NMR.
  2. bThe enantiomeric excess and conversion were determined by CD and UV sensing at 376 and 392 nm, respectively. Cat. load. catalyst loading, Conv. conversion