Skip to main content
. 2019 Nov 25;11(3):684–693. doi: 10.1039/c9sc04858h

Screening of the catalysts for the asymmetric alkylation of N-methylindole 3a with α,β-unsaturated 2-acyl imidazole 4aa.

graphic file with name c9sc04858h-u1.jpg
Entry Cat. Solvent/T (°C) T (h) % Yb % eec
1 1a CH2Cl2/25 3 90 65
2d 1a CH2Cl2/25 4 92 60
3e 1a CH2Cl2/25 5 88 58
4 1a CH2Cl2/5 10 91 73
5 1b CH2Cl2/5 10 98 79
6 1c CH2Cl2/5 15 90 69
7 1d CH2Cl2/5 12 87 57
8 1e CH2Cl2/5 10 99 85
9 1f CH2Cl2/5 10 94 71
10 1e CH2Cl2/−15 24 95 90
11 1e ClCH2CH2Cl/−15 24 97 93
12 1e CH3Cl/−15 24 96 91
13 1e CH3CN/−15 20 92 95
14 1e CH3CN/−25 48 91 97.5
a

Reaction conditions: 3a (0.45 mmol), 4a (0.3 mmol), 1 (5 mol%), 4 Å MS (100 mg) and solvent (3 mL), under argon.

b

Isolated yield.

c

Determined by chiral-phase HPLC.

d

Without 4 Å MS.

e

Without 4 Å MS, under air.