Table 2 Kinetic resolution of racemic 1p with chiral spiro phosphoramidesa

From: Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement

View full size image

Entry

Cat.

Solvent

Yield (%)b

E.r.c

1

1

PhCl

47

65:35

2

2

PhCl

44

86.5:13.5

3

3

PhCl

45

90:10

4

4

PhCl

10

58:42

5

3

Et2O

42

95:5

  1. HPLC high-performance liquid chromatography
  2. aReaction conditions: 1p (0.1 mmol), Cat. (0.02 mmol), solvent (2 mL), 25 °C, 8 h, then Et3N (0.03 mmol), PhCl (1 mL), 60 °C, 24 h, in vials
  3. bIsolated yields
  4. cDetermined by HPLC analysis on a chiral stationary phase
Back to article page