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. 2021 Jun 22;12(29):9991–9997. doi: 10.1039/d1sc02681j

Optimization of Lewis acids for the sequential reactiona.

graphic file with name d1sc02681j-u2.jpg
Entry Metal salt Yieldbb (%) 3aa : 4aac ee of 4aac (%)
1 Ni(OTf)2 76 82 : 18 92
2 Zn(OTf)2 54 6 : 94 91
3 Mg(OTf)2 52 34 : 66 91
4 Cu(OTf)2 49 1 : 99 93
5dd Cu(OTf)2 70 1 : 99 93
6ee Cu(OTf)2 70 1 : 99 93
a

Unless otherwise noted, all reactions were initially carried out with 1a (0.05 mmol), 2a (1.2 equiv.), L5-RaPr2 (10 mol%) and Ni(OTf)2 (10 mol%) in CH2Cl2 (0.2 M) at 35 °C for 16 h. Then, the metal salt (5 mol%) in CH2Cl2 (0.1 M) was added and stirred at 30 °C for 16 h under air.

b

Isolated yield of 4aa based on 1a.

c

Determined by HPLC on a chiral stationary phase.

d

4 Å MS (10 mg) in CHCl3 (0.05 M) was used for the second transformation for 3 h.

e

Isolated 3aa was treated with Cu(OTf)2 (5 mol%) and 4 Å MS (10 mg) in CHCl3 (0.05 M) at 30 °C for 4 h under N2.