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. 2021 Apr 26;12(21):7561–7568. doi: 10.1039/d1sc01029h

Initial results of the Michael reactiona.

Entry Catalyst Time (h) NMR yield of 3ab (%) d.r.c eed (%)
1 48 NR ND ND
2 A 48 89 85 : 15 −39/−40
3 B 22 84 87 : 13 40/43
4 C e 24 48 77 : 23 26/28
5 B e 24 86 85 : 15 45/46
a

Unless otherwise noted, all reactions were carried out with 0.1 mmol of 1a, 0.2 mmol of 2, and 0.02 mmol of catalyst in 0.2 mL of DCM at RT; NR – no reaction, ND – not determined.

b

Relative amount of 3a compared to the total amount of 1a, 3a and 5; determined from the reaction mixture by 1H NMR spectroscopy.

c

Determined from the reaction mixture by 1H NMR spectroscopy.

d

Determined by HPLC analysis on a chiral stationary phase.

e

10 mol% of catalyst instead of 20 mol% and (MeO)3C6H3 was used as an internal standard.