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. Author manuscript; available in PMC: 2016 Dec 23.
Published in final edited form as: J Am Chem Soc. 2015 Dec 14;137(50):15940–15946. doi: 10.1021/jacs.5b11248

Table 3.

Optimization with α,β-unsaturated imine 1j a

graphic file with name nihms782649t18.jpg
entry L x T (°C) yieldb drc eed
1 L1 10 4 88% 9 : 1 75%
2 L1 10 −10 68% 9 : 1 77%
3 L1 5 4 60% 10 : 1 74%
4 L2 10 4 96% 9 : 1 88%
5 L3 10 4 75% 7 : 1 77%
6 L4 10 4 85% 8 : 1 82%
7 L5 10 4 63% 8 : 1 65%
8 L6 10 4 80% 9 : 1 70%
a

Reaction conditions: : 0.24 mmol 1, x mol% L, 2x mol% Et2Zn (1.0 M in hexanes), 4 Å molecular sieves (10 mg), in THF (0.3 M) at the indicated temperature for 8 h.

b

Isolated yield.

c

Determined by 1H-NMR analysis.

d

Determined by HPLC on a chiral stationary phase.