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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 3.

Substrate scope of CuH-catalyzed enantioselective C3-alkylation.a

graphic file with name nihms-1014732-t0004.jpg
a

Conditions: 1 (1.0 mmol), 2d (0.50 mmol), Et3COH (0.10 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. The ee was determined by SFC analysis. The regioisomeric ratio (rr) was determined by 1H NMR analysis of the crude reaction mixture. DMMS = (MeO)2MeSiH.

b

Using 5.0 mol% Cu(OAc)2 and 6.0 mol% (S,S)-Ph-BPE instead of 1.0 mol% Cu(OAc)2 and 1.2 mol% (S,S)-Ph-BPE.