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. Author manuscript; available in PMC: 2020 Mar 6.
Published in final edited form as: J Am Chem Soc. 2019 Feb 20;141(9):3901–3909. doi: 10.1021/jacs.8b11838

Table 1.

Optimization of CuH-catalyzed enantioselective N- and C3-alkylation of indole derivatives.a

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a

Reactions were conducted on 0.10 mmol scale. Yields were determined by gas chromatography using dodecane as internal standard.

b

The ee was determined by SFC analysis.

c

The regioisomeric ratio (rr) was determined by GC analysis of the crude reaction mixture.

d

Conditions: 1 (0.10 mmol), 2 (0.10 mmol), Cu(OAc)2 (5.0 mol%), (R)-DTBM-SEGPHOS (6.0 mol%), DEMS (4.0 equiv), THF (0.1 M), 90 °C, 12 h.

e

Conditions: 1 (0.15 mmol), 2 (0.10 mmol), Cu(OAc)2 (5.0 mol%), ligand (6.0 mol%), DEMS (4.0 equiv), THF (0.5 M), 50 °C, 12 h.

f

Conditions: 1 (0.10 mmol), 2 (0.15 mmol), Et3COH (0.02 mmol), Cu(OAc)2 (5.0 mol%), (R)-DTBM-SEGPHOS (6.0 mol%), DEMS (4.0 equiv), THF (0.1 M), 90 °C, 20 h.

g

Isolated yield on a 0.50 mmol scale.

h

Conditions: 1 (0.20 mmol), 2d (0.10 mmol), Et3COH (0.02 mmol), Cu(OAc)2 (1.0 mol%), (S,S)-Ph-BPE (1.2 mol%), DMMS (4.0 equiv), THF (0.5 M), 40 °C, 24 h. ND = Not determined. DEMS = (EtO)2MeSiH. DMMS = (MeO)2MeSiH.