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. 2020 Oct 21;5(43):27978–27989. doi: 10.1021/acsomega.0c03485

Table 3. Results of Selected Asymmetric FC Alkylation Reactions of Indoles with MTNSa.

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entry cat* R1 R2 t (min) conv.b (%) eec (%)
1 1 H H 30 55 rac
2 2     30 22 –2
3 1 Me H 30 90 +12
4 2     30 43 +15
5 1 H Me 30 81 +3
6 2     30 48 +15
7 1 Me Me 5 100 +93
8 2     30 100 –21
a

Reagents and conditions: catalyst (0.03 mmol, 5.0 mol %), MTNS (0.90 mmol), indole (0.60 mmol), 4 Å molecular sieves (100 mg), and CH2Cl2 (4 mL).

b

Based on indole. Determined by 1H NMR spectroscopy.

c

Determined by high-performance liquid chromatography (HPLC). Changes in the sign indicate that the opposite enantiomer was preferentially obtained.