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. 2021 Oct 20;12(44):14863–14870. doi: 10.1039/d1sc04299h

Optimization of reaction conditionsa.

graphic file with name d1sc04299h-u1.jpg
(b) Additive screening
Entry Additives C b eec (%) s d
(R)-1a-1 (S)-3a-1
1 BQ 18 17 78 10
2 2-Chloro BQ 39 50 77 13
3 2,5-dichloro BQ 35 40 75 10
a

Reaction conditions:rac-1a-1 (0.1 mmol), ethyl acrylate 2a (0.6 equiv.), Pd(OAc)2 (10 mol%), ligand (30 mol%), Ag2CO3 (2.0 equiv.), 2-Cl-BQ (0.3 equiv.), 1,2-DCE (1.0 mL), N2, 75 °C, 3 days.

b

Calculated conversion, C = eeSM/(eeSM + eePR).

c

Determined by chiral HPLC analysis.

d

Selectivity (s) = ln[(1 − C)(1 − eeSM)]/ln[(1 − C)(1 + eeSM)].

e

2a (2.0 equiv.) used.